diff --git a/.github/workflows/tauri-build.yml b/.github/workflows/tauri-build.yml
index 4c833bc16..09ef22a16 100644
--- a/.github/workflows/tauri-build.yml
+++ b/.github/workflows/tauri-build.yml
@@ -14,7 +14,7 @@ on:
           - macos
           - linux
   pull_request:
-    branches: [main, V2]
+    branches: [main, V2, V2-tauri-windows]
     paths:
       - 'frontend/src-tauri/**'
       - 'frontend/src/desktop/**'
@@ -61,6 +61,9 @@ jobs:
       fail-fast: false
       matrix: ${{ fromJson(needs.determine-matrix.outputs.matrix) }}
     runs-on: ${{ matrix.platform }}
+    env:
+      SM_API_KEY: ${{ secrets.SM_API_KEY }}
+      WINDOWS_CERTIFICATE: ${{ secrets.WINDOWS_CERTIFICATE }}
     steps:
       - name: Harden Runner
         uses: step-security/harden-runner@002fdce3c6a235733a90a27c80493a3241e56863 # v2.12.1
@@ -174,6 +177,84 @@ jobs:
         working-directory: ./frontend
         run: npm install
 
+      # DigiCert KeyLocker Setup (Cloud HSM)
+      - name: Setup DigiCert KeyLocker
+        id: digicert-setup
+        if: ${{ matrix.platform == 'windows-latest' && env.SM_API_KEY != '' }}
+        uses: digicert/ssm-code-signing@v1.1.0
+        env:
+          SM_API_KEY: ${{ secrets.SM_API_KEY }}
+          SM_CLIENT_CERT_FILE_B64: ${{ secrets.SM_CLIENT_CERT_FILE_B64 }}
+          SM_CLIENT_CERT_PASSWORD: ${{ secrets.SM_CLIENT_CERT_PASSWORD }}
+          SM_KEYPAIR_ALIAS: ${{ secrets.SM_KEYPAIR_ALIAS }}
+          SM_HOST: ${{ secrets.SM_HOST }}
+
+      - name: Setup DigiCert KeyLocker Certificate
+        if: ${{ matrix.platform == 'windows-latest' && env.SM_API_KEY != '' }}
+        shell: pwsh
+        run: |
+          Write-Host "Setting up DigiCert KeyLocker environment..."
+
+          # Decode client certificate
+          $certBytes = [Convert]::FromBase64String("${{ secrets.SM_CLIENT_CERT_FILE_B64 }}")
+          $certPath = "D:\Certificate_pkcs12.p12"
+          [IO.File]::WriteAllBytes($certPath, $certBytes)
+
+          # Set environment variables
+          echo "SM_CLIENT_CERT_FILE=D:\Certificate_pkcs12.p12" >> $env:GITHUB_ENV
+          echo "SM_HOST=${{ secrets.SM_HOST }}" >> $env:GITHUB_ENV
+          echo "SM_API_KEY=${{ secrets.SM_API_KEY }}" >> $env:GITHUB_ENV
+          echo "SM_CLIENT_CERT_PASSWORD=${{ secrets.SM_CLIENT_CERT_PASSWORD }}" >> $env:GITHUB_ENV
+          echo "SM_KEYPAIR_ALIAS=${{ secrets.SM_KEYPAIR_ALIAS }}" >> $env:GITHUB_ENV
+
+          # Get PKCS11 config path from DigiCert action
+          $pkcs11Config = $env:PKCS11_CONFIG
+          if ($pkcs11Config) {
+            Write-Host "Found PKCS11_CONFIG: $pkcs11Config"
+            echo "PKCS11_CONFIG=$pkcs11Config" >> $env:GITHUB_ENV
+          } else {
+            Write-Host "PKCS11_CONFIG not set by DigiCert action, using default path"
+            $defaultPath = "C:\Users\RUNNER~1\AppData\Local\Temp\smtools-windows-x64\pkcs11properties.cfg"
+            if (Test-Path $defaultPath) {
+              Write-Host "Found config at default path: $defaultPath"
+              echo "PKCS11_CONFIG=$defaultPath" >> $env:GITHUB_ENV
+            } else {
+              Write-Host "Warning: Could not find PKCS11 config file"
+            }
+          }
+
+      # Traditional PFX Certificate Import (fallback if KeyLocker not configured)
+      - name: Import Windows Code Signing Certificate
+        if: ${{ matrix.platform == 'windows-latest' && env.SM_API_KEY == '' }}
+        env:
+          WINDOWS_CERTIFICATE: ${{ secrets.WINDOWS_CERTIFICATE }}
+          WINDOWS_CERTIFICATE_PASSWORD: ${{ secrets.WINDOWS_CERTIFICATE_PASSWORD }}
+        shell: powershell
+        run: |
+          if ($env:WINDOWS_CERTIFICATE) {
+            Write-Host "Importing Windows Code Signing Certificate..."
+
+            # Decode base64 certificate and save to file
+            $certBytes = [Convert]::FromBase64String($env:WINDOWS_CERTIFICATE)
+            $certPath = Join-Path $env:RUNNER_TEMP "certificate.pfx"
+            [IO.File]::WriteAllBytes($certPath, $certBytes)
+
+            # Import certificate to CurrentUser\My store
+            $cert = Import-PfxCertificate -FilePath $certPath -CertStoreLocation Cert:\CurrentUser\My -Password (ConvertTo-SecureString -String $env:WINDOWS_CERTIFICATE_PASSWORD -AsPlainText -Force)
+
+            # Extract and set thumbprint as environment variable
+            $thumbprint = $cert.Thumbprint
+            Write-Host "Certificate imported with thumbprint: $thumbprint"
+            echo "WINDOWS_CERTIFICATE_THUMBPRINT=$thumbprint" >> $env:GITHUB_ENV
+
+            # Clean up certificate file
+            Remove-Item $certPath
+
+            Write-Host "Windows certificate import completed."
+          } else {
+            Write-Host "⚠️ WINDOWS_CERTIFICATE secret not set - building unsigned binary"
+          }
+
       - name: Import Apple Developer Certificate
         if: matrix.platform == 'macos-15' || matrix.platform == 'macos-15-intel'
         env:
@@ -229,13 +310,174 @@ jobs:
           APPLE_PASSWORD: ${{ secrets.APPLE_ID_PASSWORD }}
           APPLE_TEAM_ID: ${{ secrets.APPLE_TEAM_ID }}
           APPIMAGETOOL_SIGN_PASSPHRASE: ${{ secrets.APPIMAGETOOL_SIGN_PASSPHRASE }}
-          SIGN: 1
+          TAURI_SIGNING_PRIVATE_KEY: ${{ secrets.TAURI_SIGNING_PRIVATE_KEY }}
+          TAURI_SIGNING_PRIVATE_KEY_PASSWORD: ${{ secrets.TAURI_SIGNING_PRIVATE_KEY_PASSWORD }}
+          SIGN: ${{ (env.SM_API_KEY == '' && env.WINDOWS_CERTIFICATE != '') && '1' || '0' }}
           CI: true
         with:
           projectPath: ./frontend
           tauriScript: npx tauri
           args: ${{ matrix.args }}
 
+      # Sign with DigiCert KeyLocker (post-build)
+      - name: Sign Windows binaries with DigiCert KeyLocker
+        if: ${{ matrix.platform == 'windows-latest' && env.SM_API_KEY != '' }}
+        shell: pwsh
+        run: |
+          Write-Host "=== DigiCert KeyLocker Signing ==="
+
+          # Test smctl connectivity first
+          Write-Host "Testing smctl connection..."
+          $healthCheck = & smctl healthcheck 2>&1
+          if ($LASTEXITCODE -eq 0) {
+            Write-Host "[SUCCESS] Connected to DigiCert KeyLocker"
+          } else {
+            Write-Host "[ERROR] Failed to connect to DigiCert KeyLocker"
+            Write-Host $healthCheck
+            exit 1
+          }
+          Write-Host ""
+
+          # Sync certificates to Windows certificate store
+          Write-Host "Syncing certificates to Windows certificate store..."
+          $syncOutput = & smctl windows certsync 2>&1
+          Write-Host "Cert sync result: $syncOutput"
+          Write-Host ""
+
+          # List available certificates and check if they have certificates attached
+          Write-Host "Checking for available certificates..."
+          $certList = & smctl keypair ls 2>&1
+          Write-Host "Keypair list output:"
+          Write-Host $certList
+          Write-Host ""
+
+          # Parse the output to check certificate status
+          $lines = $certList -split "`n"
+          $foundKeypair = $false
+          $hasCertificate = $false
+
+          foreach ($line in $lines) {
+            if ($line -match "${{ secrets.SM_KEYPAIR_ALIAS }}") {
+              $foundKeypair = $true
+              Write-Host "[SUCCESS] Found keypair in list"
+
+              # Check if this line has certificate info (not just empty spaces after alias)
+              $parts = $line -split "\s+"
+              if ($parts.Count -gt 2 -and $parts[1] -ne "" -and $parts[1] -ne "CERTIFICATE") {
+                $hasCertificate = $true
+                Write-Host "[SUCCESS] Certificate is associated with keypair"
+              }
+            }
+          }
+
+          if (-not $foundKeypair) {
+            Write-Host "[ERROR] Keypair not found: ${{ secrets.SM_KEYPAIR_ALIAS }}"
+            Write-Host "Available keypairs are listed above"
+            Write-Host ""
+            Write-Host "Please verify:"
+            Write-Host "  1. Keypair alias is correct in GitHub secret"
+            Write-Host "  2. API key has access to this keypair"
+            exit 1
+          }
+
+          if (-not $hasCertificate) {
+            Write-Host "[ERROR] No certificate associated with keypair"
+            Write-Host "This usually means:"
+            Write-Host "  1. Certificate not yet synced to KeyLocker (run sync manually)"
+            Write-Host "  2. Certificate is pending approval"
+            Write-Host "  3. Certificate needs to be attached to the keypair"
+            Write-Host ""
+            Write-Host "Try running in DigiCert ONE portal:"
+            Write-Host "  smctl keypair sync"
+            exit 1
+          }
+
+          Write-Host "[SUCCESS] Certificate check passed"
+          Write-Host ""
+
+          # Find only the files we need to sign (not build scripts)
+          $filesToSign = @()
+
+          # Main application executable
+          $mainExe = Get-ChildItem -Path "./frontend/src-tauri/target/x86_64-pc-windows-msvc/release" -Filter "stirling-pdf.exe" -File -ErrorAction SilentlyContinue
+          if ($mainExe) { $filesToSign += $mainExe }
+
+          # MSI installer
+          $msiFiles = Get-ChildItem -Path "./frontend/src-tauri/target" -Filter "*.msi" -Recurse -File
+          $filesToSign += $msiFiles
+
+          if ($filesToSign.Count -eq 0) {
+            Write-Host "[ERROR] No files found to sign"
+            exit 1
+          }
+
+          Write-Host "Found $($filesToSign.Count) files to sign:"
+          foreach ($f in $filesToSign) { Write-Host "  - $($f.Name)" }
+          Write-Host ""
+
+          $signedCount = 0
+          foreach ($file in $filesToSign) {
+            Write-Host "Signing: $($file.Name)"
+
+            # Get PKCS11 config file path (set by DigiCert action)
+            $pkcs11Config = $env:PKCS11_CONFIG
+            if (-not $pkcs11Config) {
+              Write-Host "[ERROR] PKCS11_CONFIG environment variable not set"
+              Write-Host "DigiCert KeyLocker action may not have run correctly"
+              exit 1
+            }
+
+            Write-Host "Using PKCS11 config: $pkcs11Config"
+
+            # Try signing with certificate fingerprint first (if available)
+            $fingerprint = "${{ secrets.SM_CODE_SIGNING_CERT_SHA1_HASH }}"
+            if ($fingerprint -and $fingerprint -ne "") {
+              Write-Host "Attempting to sign with certificate fingerprint..."
+              $output = & smctl sign --fingerprint "$fingerprint" --input "$($file.FullName)" --config-file "$pkcs11Config" --verbose 2>&1
+              $exitCode = $LASTEXITCODE
+            } else {
+              Write-Host "No fingerprint provided, using keypair alias..."
+              # Use smctl to sign with keypair alias
+              $output = & smctl sign --keypair-alias "${{ secrets.SM_KEYPAIR_ALIAS }}" --input "$($file.FullName)" --config-file "$pkcs11Config" --verbose 2>&1
+              $exitCode = $LASTEXITCODE
+            }
+
+            Write-Host "Exit code: $exitCode"
+            Write-Host "Output: $output"
+
+            # Check if output contains "FAILED" even with exit code 0
+            if ($output -match "FAILED" -or $output -match "error" -or $output -match "Error") {
+              Write-Host ""
+              Write-Host "[ERROR] Signing failed for $($file.Name)"
+              Write-Host "[ERROR] smctl returned success but output indicates failure"
+              Write-Host ""
+              Write-Host "Possible issues:"
+              Write-Host "  1. Certificate not fully synced to KeyLocker (wait a few minutes)"
+              Write-Host "  2. Incorrect keypair alias"
+              Write-Host "  3. API key lacks signing permissions"
+              Write-Host ""
+              Write-Host "Please verify in DigiCert ONE portal:"
+              Write-Host "  - Certificate status is 'Issued' (not Pending)"
+              Write-Host "  - Keypair status is 'Online'"
+              Write-Host "  - 'Can sign' is set to 'Yes'"
+              exit 1
+            }
+
+            if ($exitCode -ne 0) {
+              Write-Host "[ERROR] Failed to sign $($file.Name)"
+              Write-Host "Full error output:"
+              Write-Host $output
+              exit 1
+            }
+
+            $signedCount++
+            Write-Host "[SUCCESS] Signed: $($file.Name)"
+            Write-Host ""
+          }
+
+          Write-Host "=== Summary ==="
+          Write-Host "[SUCCESS] Signed $signedCount/$($filesToSign.Count) files successfully"
+
       - name: Verify notarization (macOS only)
         if: matrix.platform == 'macos-15' || matrix.platform == 'macos-15-intel'
         run: |
@@ -269,6 +511,66 @@ jobs:
             find . -name "*.AppImage" -exec cp {} "../../../dist/Stirling-PDF-${{ matrix.name }}.AppImage" \;
           fi
 
+      - name: Verify Windows Code Signature
+        if: matrix.platform == 'windows-latest'
+        shell: pwsh
+        run: |
+          Write-Host "Verifying Windows code signatures..."
+
+          $exePath = "./dist/Stirling-PDF-${{ matrix.name }}.exe"
+          $msiPath = "./dist/Stirling-PDF-${{ matrix.name }}.msi"
+
+          $allSigned = $true
+          $usingKeyLocker = "${{ env.SM_API_KEY }}" -ne ""
+          $usingPfx = "${{ env.WINDOWS_CERTIFICATE }}" -ne ""
+
+          # Check EXE signature
+          if (Test-Path $exePath) {
+            $exeSig = Get-AuthenticodeSignature -FilePath $exePath
+            Write-Host "EXE Signature Status: $($exeSig.Status)"
+            Write-Host "EXE Signer: $($exeSig.SignerCertificate.Subject)"
+            Write-Host "EXE Timestamp: $($exeSig.TimeStamperCertificate.NotAfter)"
+
+            if ($exeSig.Status -ne "Valid") {
+              Write-Host "[WARNING] EXE is not properly signed (Status: $($exeSig.Status))"
+              if ($usingKeyLocker -or $usingPfx) {
+                Write-Host "[ERROR] Certificate was provided but signing failed"
+                $allSigned = $false
+              } else {
+                Write-Host "[INFO] Building unsigned binary (no certificate provided)"
+              }
+            } else {
+              Write-Host "[SUCCESS] EXE is properly signed"
+            }
+          }
+
+          # Check MSI signature
+          if (Test-Path $msiPath) {
+            $msiSig = Get-AuthenticodeSignature -FilePath $msiPath
+            Write-Host "MSI Signature Status: $($msiSig.Status)"
+            Write-Host "MSI Signer: $($msiSig.SignerCertificate.Subject)"
+            Write-Host "MSI Timestamp: $($msiSig.TimeStamperCertificate.NotAfter)"
+
+            if ($msiSig.Status -ne "Valid") {
+              Write-Host "[WARNING] MSI is not properly signed (Status: $($msiSig.Status))"
+              if ($usingKeyLocker -or $usingPfx) {
+                Write-Host "[ERROR] Certificate was provided but signing failed"
+                $allSigned = $false
+              } else {
+                Write-Host "[INFO] Building unsigned binary (no certificate provided)"
+              }
+            } else {
+              Write-Host "[SUCCESS] MSI is properly signed"
+            }
+          }
+
+          if (($usingKeyLocker -or $usingPfx) -and -not $allSigned) {
+            Write-Host "[ERROR] Code signing verification failed"
+            exit 1
+          } else {
+            Write-Host "[SUCCESS] Code signature verification completed"
+          }
+
       - name: Upload artifacts
         uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
         with:
diff --git a/README.md b/README.md
index 211301b99..1d7188998 100644
--- a/README.md
+++ b/README.md
@@ -115,46 +115,46 @@ Stirling-PDF currently supports 40 languages!
 
 | Language                                     | Progress                               |
 | -------------------------------------------- | -------------------------------------- |
-| Arabic (العربية) (ar_AR)                        | ![64%](https://geps.dev/progress/64)   |
-| Azerbaijani (Azərbaycan Dili) (az_AZ)        | ![24%](https://geps.dev/progress/24)   |
-| Basque (Euskara) (eu_ES)                     | ![14%](https://geps.dev/progress/14)   |
-| Bulgarian (Български) (bg_BG)                | ![26%](https://geps.dev/progress/26)   |
-| Catalan (Català) (ca_CA)                     | ![26%](https://geps.dev/progress/26)   |
-| Croatian (Hrvatski) (hr_HR)                  | ![24%](https://geps.dev/progress/24)   |
-| Czech (Česky) (cs_CZ)                        | ![26%](https://geps.dev/progress/26)   |
-| Danish (Dansk) (da_DK)                       | ![23%](https://geps.dev/progress/23)   |
-| Dutch (Nederlands) (nl_NL)                   | ![23%](https://geps.dev/progress/23)   |
+| Arabic (العربية) (ar_AR)                        | ![94%](https://geps.dev/progress/94)   |
+| Azerbaijani (Azərbaycan Dili) (az_AZ)        | ![93%](https://geps.dev/progress/93)   |
+| Basque (Euskara) (eu_ES)                     | ![93%](https://geps.dev/progress/93)   |
+| Bulgarian (Български) (bg_BG)                | ![94%](https://geps.dev/progress/94)   |
+| Catalan (Català) (ca_CA)                     | ![93%](https://geps.dev/progress/93)   |
+| Croatian (Hrvatski) (hr_HR)                  | ![93%](https://geps.dev/progress/93)   |
+| Czech (Česky) (cs_CZ)                        | ![91%](https://geps.dev/progress/91)   |
+| Danish (Dansk) (da_DK)                       | ![92%](https://geps.dev/progress/92)   |
+| Dutch (Nederlands) (nl_NL)                   | ![93%](https://geps.dev/progress/93)   |
 | English (English) (en_GB)                    | ![100%](https://geps.dev/progress/100) |
 | English (US) (en_US)                         | ![100%](https://geps.dev/progress/100) |
-| French (Français) (fr_FR)                    | ![63%](https://geps.dev/progress/63)   |
-| German (Deutsch) (de_DE)                     | ![64%](https://geps.dev/progress/64)   |
-| Greek (Ελληνικά) (el_GR)                     | ![26%](https://geps.dev/progress/26)   |
-| Hindi (हिंदी) (hi_IN)                          | ![26%](https://geps.dev/progress/26)   |
-| Hungarian (Magyar) (hu_HU)                   | ![29%](https://geps.dev/progress/29)   |
-| Indonesian (Bahasa Indonesia) (id_ID)        | ![24%](https://geps.dev/progress/24)   |
-| Irish (Gaeilge) (ga_IE)                      | ![26%](https://geps.dev/progress/26)   |
-| Italian (Italiano) (it_IT)                   | ![64%](https://geps.dev/progress/64)   |
-| Japanese (日本語) (ja_JP)                    | ![47%](https://geps.dev/progress/47)   |
-| Korean (한국어) (ko_KR)                      | ![26%](https://geps.dev/progress/26)   |
-| Norwegian (Norsk) (no_NB)                    | ![24%](https://geps.dev/progress/24)   |
-| Persian (فارسی) (fa_IR)                      | ![26%](https://geps.dev/progress/26)   |
-| Polish (Polski) (pl_PL)                      | ![27%](https://geps.dev/progress/27)   |
-| Portuguese (Português) (pt_PT)               | ![26%](https://geps.dev/progress/26)   |
-| Portuguese Brazilian (Português) (pt_BR)     | ![64%](https://geps.dev/progress/64)   |
-| Romanian (Română) (ro_RO)                    | ![22%](https://geps.dev/progress/22)   |
-| Russian (Русский) (ru_RU)                    | ![63%](https://geps.dev/progress/63)   |
-| Serbian Latin alphabet (Srpski) (sr_LATN_RS) | ![28%](https://geps.dev/progress/28)   |
-| Simplified Chinese (简体中文) (zh_CN)         | ![65%](https://geps.dev/progress/65)   |
-| Slovakian (Slovensky) (sk_SK)                | ![19%](https://geps.dev/progress/19)   |
-| Slovenian (Slovenščina) (sl_SI)              | ![27%](https://geps.dev/progress/27)   |
-| Spanish (Español) (es_ES)                    | ![64%](https://geps.dev/progress/64)   |
-| Swedish (Svenska) (sv_SE)                    | ![25%](https://geps.dev/progress/25)   |
-| Thai (ไทย) (th_TH)                           | ![23%](https://geps.dev/progress/23)   |
+| French (Français) (fr_FR)                    | ![93%](https://geps.dev/progress/93)   |
+| German (Deutsch) (de_DE)                     | ![93%](https://geps.dev/progress/93)   |
+| Greek (Ελληνικά) (el_GR)                     | ![93%](https://geps.dev/progress/93)   |
+| Hindi (हिंदी) (hi_IN)                          | ![94%](https://geps.dev/progress/94)   |
+| Hungarian (Magyar) (hu_HU)                   | ![94%](https://geps.dev/progress/94)   |
+| Indonesian (Bahasa Indonesia) (id_ID)        | ![93%](https://geps.dev/progress/93)   |
+| Irish (Gaeilge) (ga_IE)                      | ![94%](https://geps.dev/progress/94)   |
+| Italian (Italiano) (it_IT)                   | ![93%](https://geps.dev/progress/93)   |
+| Japanese (日本語) (ja_JP)                    | ![94%](https://geps.dev/progress/94)   |
+| Korean (한국어) (ko_KR)                      | ![94%](https://geps.dev/progress/94)   |
+| Norwegian (Norsk) (no_NB)                    | ![93%](https://geps.dev/progress/93)   |
+| Persian (فارسی) (fa_IR)                      | ![94%](https://geps.dev/progress/94)   |
+| Polish (Polski) (pl_PL)                      | ![93%](https://geps.dev/progress/93)   |
+| Portuguese (Português) (pt_PT)               | ![93%](https://geps.dev/progress/93)   |
+| Portuguese Brazilian (Português) (pt_BR)     | ![93%](https://geps.dev/progress/93)   |
+| Romanian (Română) (ro_RO)                    | ![93%](https://geps.dev/progress/93)   |
+| Russian (Русский) (ru_RU)                    | ![94%](https://geps.dev/progress/94)   |
+| Serbian Latin alphabet (Srpski) (sr_LATN_RS) | ![93%](https://geps.dev/progress/93)   |
+| Simplified Chinese (简体中文) (zh_CN)         | ![94%](https://geps.dev/progress/94)   |
+| Slovakian (Slovensky) (sk_SK)                | ![93%](https://geps.dev/progress/93)   |
+| Slovenian (Slovenščina) (sl_SI)              | ![94%](https://geps.dev/progress/94)   |
+| Spanish (Español) (es_ES)                    | ![94%](https://geps.dev/progress/94)   |
+| Swedish (Svenska) (sv_SE)                    | ![93%](https://geps.dev/progress/93)   |
+| Thai (ไทย) (th_TH)                           | ![93%](https://geps.dev/progress/93)   |
 | Tibetan (བོད་ཡིག་) (bo_CN)                     | ![65%](https://geps.dev/progress/65) |
-| Traditional Chinese (繁體中文) (zh_TW)        | ![29%](https://geps.dev/progress/29)   |
-| Turkish (Türkçe) (tr_TR)                     | ![28%](https://geps.dev/progress/28)   |
-| Ukrainian (Українська) (uk_UA)               | ![28%](https://geps.dev/progress/28)   |
-| Vietnamese (Tiếng Việt) (vi_VN)              | ![21%](https://geps.dev/progress/21)   |
+| Traditional Chinese (繁體中文) (zh_TW)        | ![94%](https://geps.dev/progress/94)   |
+| Turkish (Türkçe) (tr_TR)                     | ![94%](https://geps.dev/progress/94)   |
+| Ukrainian (Українська) (uk_UA)               | ![94%](https://geps.dev/progress/94)   |
+| Vietnamese (Tiếng Việt) (vi_VN)              | ![93%](https://geps.dev/progress/93)   |
 | Malayalam (മലയാളം) (ml_IN)              | ![73%](https://geps.dev/progress/73)   |
 
 ## Stirling PDF Enterprise
diff --git a/WINDOWS_SIGNING.md b/WINDOWS_SIGNING.md
new file mode 100644
index 000000000..45528e13a
--- /dev/null
+++ b/WINDOWS_SIGNING.md
@@ -0,0 +1,258 @@
+# Windows Code Signing Setup Guide
+
+This guide explains how to set up Windows code signing for Stirling-PDF desktop application builds.
+
+## Overview
+
+Windows code signing is essential for:
+- Preventing Windows SmartScreen warnings
+- Building trust with users
+- Enabling Microsoft Store distribution
+- Professional application distribution
+
+## Certificate Types
+
+### OV Certificate (Organization Validated)
+- More affordable option
+- Requires business verification
+- May trigger SmartScreen warnings initially until reputation builds
+- Suitable for most independent software vendors
+
+### EV Certificate (Extended Validation)
+- Premium option with immediate SmartScreen reputation
+- Requires hardware security module (HSM) or cloud-based signing
+- Higher cost but provides immediate trust
+- Required since June 2023 for new certificates
+
+## Obtaining a Certificate
+
+### Certificate Authorities
+Popular certificate authorities for Windows code signing:
+- DigiCert
+- Sectigo (formerly Comodo)
+- GlobalSign
+- SSL.com
+
+### Certificate Format
+You'll receive a certificate in one of these formats:
+- `.pfx` or `.p12` (preferred - contains both certificate and private key)
+- `.cer` + private key (needs conversion to .pfx)
+
+### Converting to PFX (if needed)
+If you have separate certificate and private key files:
+
+```bash
+openssl pkcs12 -export -out certificate.pfx -inkey private-key.key -in certificate.cer
+```
+
+## Setting Up GitHub Secrets
+
+### Required Secrets
+
+Navigate to your GitHub repository → Settings → Secrets and variables → Actions
+
+Add the following secrets:
+
+#### 1. `WINDOWS_CERTIFICATE`
+- **Description**: Base64-encoded .pfx certificate file
+- **How to create**:
+
+**On macOS/Linux:**
+```bash
+base64 -i certificate.pfx | pbcopy  # Copies to clipboard
+```
+
+**On Windows (PowerShell):**
+```powershell
+[Convert]::ToBase64String([IO.File]::ReadAllBytes("certificate.pfx")) | Set-Clipboard
+```
+
+Paste the entire base64 string into the GitHub secret.
+
+#### 2. `WINDOWS_CERTIFICATE_PASSWORD`
+- **Description**: Password for the .pfx certificate
+- **Value**: The password you set when creating/exporting the .pfx file
+
+### Optional Secrets for Tauri Updater
+
+If you're using Tauri's built-in updater feature:
+
+#### `TAURI_SIGNING_PRIVATE_KEY`
+- Generated using Tauri CLI: `npm run tauri signer generate`
+- Used for update package verification
+
+#### `TAURI_SIGNING_PRIVATE_KEY_PASSWORD`
+- Password for the Tauri signing key
+
+## Configuration Files
+
+### 1. Tauri Configuration (frontend/src-tauri/tauri.conf.json)
+
+The Windows signing configuration is already set up:
+
+```json
+"windows": {
+  "certificateThumbprint": null,
+  "digestAlgorithm": "sha256",
+  "timestampUrl": "http://timestamp.digicert.com"
+}
+```
+
+**Configuration Options:**
+- `certificateThumbprint`: Automatically extracted from imported certificate (leave as `null`)
+- `digestAlgorithm`: Hashing algorithm - `sha256` is recommended
+- `timestampUrl`: Timestamp server to prove signing time (survives certificate expiration)
+
+**Alternative Timestamp Servers:**
+- DigiCert: `http://timestamp.digicert.com`
+- Sectigo: `http://timestamp.sectigo.com`
+- GlobalSign: `http://timestamp.globalsign.com`
+
+### 2. GitHub Workflow (.github/workflows/tauri-build.yml)
+
+The workflow includes three Windows signing steps:
+
+1. **Import Certificate**: Decodes and imports the .pfx certificate into Windows certificate store
+2. **Build Tauri App**: Builds and signs the application using the imported certificate
+3. **Verify Signature**: Validates that both .exe and .msi files are properly signed
+
+## Testing the Setup
+
+### 1. Local Testing (Windows Only)
+
+Before pushing to GitHub, test locally:
+
+```powershell
+# Set environment variables
+$env:WINDOWS_CERTIFICATE = [Convert]::ToBase64String([IO.File]::ReadAllBytes("certificate.pfx"))
+$env:WINDOWS_CERTIFICATE_PASSWORD = "your-certificate-password"
+
+# Build the application
+cd frontend
+npm run tauri build
+
+# Verify the signature
+Get-AuthenticodeSignature "./src-tauri/target/release/bundle/msi/Stirling-PDF_*.msi"
+```
+
+### 2. GitHub Actions Testing
+
+1. Push your changes to a branch
+2. Manually trigger the workflow:
+   - Go to Actions → Build Tauri Applications
+   - Click "Run workflow"
+   - Select "windows" platform
+3. Check the build logs for:
+   - ✅ Certificate import success
+   - ✅ Build completion
+   - ✅ Signature verification
+
+### 3. Verifying Signed Binaries
+
+After downloading the built artifacts:
+
+**Windows (PowerShell):**
+```powershell
+Get-AuthenticodeSignature "Stirling-PDF-windows-x86_64.exe"
+Get-AuthenticodeSignature "Stirling-PDF-windows-x86_64.msi"
+```
+
+Look for:
+- Status: `Valid`
+- Signer: Your organization name
+- Timestamp: Recent date/time
+
+**Windows (GUI):**
+1. Right-click the .exe or .msi file
+2. Select "Properties"
+3. Go to "Digital Signatures" tab
+4. Verify signature details
+
+## Troubleshooting
+
+### "HashMismatch" Status
+- Certificate doesn't match the binary
+- Possible file corruption during download
+- Re-download and verify
+
+### "NotSigned" Status
+- Certificate wasn't imported correctly
+- Check GitHub secrets are set correctly
+- Verify base64 encoding is complete (no truncation)
+
+### "UnknownError" Status
+- Timestamp server unreachable
+- Try alternative timestamp URL in tauri.conf.json
+- Check network connectivity in GitHub Actions
+
+### SmartScreen Still Shows Warnings
+- Normal for OV certificates initially
+- Reputation builds over time with user downloads
+- Consider EV certificate for immediate reputation
+
+### Certificate Not Found During Build
+- Verify `WINDOWS_CERTIFICATE` secret is set
+- Check base64 encoding is correct (no extra whitespace)
+- Ensure password is correct
+
+## Security Best Practices
+
+1. **Never commit certificates to version control**
+   - Keep .pfx files secure and backed up
+   - Use GitHub secrets for CI/CD
+
+2. **Rotate certificates before expiration**
+   - Set calendar reminders
+   - Update GitHub secrets with new certificate
+
+3. **Use strong passwords**
+   - Certificate password should be complex
+   - Store securely (password manager)
+
+4. **Monitor certificate usage**
+   - Review GitHub Actions logs
+   - Set up notifications for failed builds
+
+5. **Limit access to secrets**
+   - Only repository admins should access secrets
+   - Audit secret access regularly
+
+## Certificate Lifecycle
+
+### Before Expiration
+1. Obtain new certificate from CA (typically annual renewal)
+2. Convert to .pfx format if needed
+3. Update `WINDOWS_CERTIFICATE` secret with new base64-encoded certificate
+4. Update `WINDOWS_CERTIFICATE_PASSWORD` if password changed
+5. Test build to verify new certificate works
+
+### Expired Certificates
+- Signed binaries remain valid (timestamp proves signing time)
+- New builds will fail until certificate is renewed
+- Users can still install previously signed versions
+
+## Cost Considerations
+
+### Certificate Costs (Annual, as of 2024)
+- **OV Certificate**: $100-400/year
+- **EV Certificate**: $400-1000/year
+
+### Choosing the Right Certificate
+- **Open source / early stage**: Start with OV
+- **Commercial / enterprise**: Consider EV for better trust
+- **Microsoft Store**: EV certificate required
+
+## Additional Resources
+
+- [Tauri Windows Signing Documentation](https://v2.tauri.app/distribute/sign/windows/)
+- [Microsoft Code Signing Overview](https://docs.microsoft.com/windows/win32/seccrypto/cryptography-tools)
+- [DigiCert Code Signing Guide](https://www.digicert.com/signing/code-signing-certificates)
+- [Windows SmartScreen FAQ](https://support.microsoft.com/windows/smartscreen-faq)
+
+## Support
+
+If you encounter issues with Windows code signing:
+1. Check GitHub Actions logs for detailed error messages
+2. Verify all secrets are set correctly
+3. Test certificate locally first (Windows environment required)
+4. Open an issue in the repository with relevant logs (remove sensitive data)
diff --git a/app/core/src/main/java/stirling/software/SPDF/SPDFApplication.java b/app/core/src/main/java/stirling/software/SPDF/SPDFApplication.java
index 587bc992e..d3a4ce776 100644
--- a/app/core/src/main/java/stirling/software/SPDF/SPDFApplication.java
+++ b/app/core/src/main/java/stirling/software/SPDF/SPDFApplication.java
@@ -12,6 +12,8 @@ import java.util.Properties;
 
 import org.springframework.boot.SpringApplication;
 import org.springframework.boot.autoconfigure.SpringBootApplication;
+import org.springframework.boot.web.context.WebServerInitializedEvent;
+import org.springframework.context.event.EventListener;
 import org.springframework.core.env.Environment;
 import org.springframework.scheduling.annotation.EnableScheduling;
 
@@ -198,6 +200,14 @@ public class SPDFApplication {
         // }
     }
 
+    @EventListener
+    public void onWebServerInitialized(WebServerInitializedEvent event) {
+        int actualPort = event.getWebServer().getPort();
+        serverPortStatic = String.valueOf(actualPort);
+        // Log the actual runtime port for Tauri to parse
+        log.info("Stirling-PDF running on port: {}", actualPort);
+    }
+
     private static void printStartupLogs() {
         log.info("Stirling-PDF Started.");
         String url = baseUrlStatic + ":" + getStaticPort() + contextPathStatic;
diff --git a/app/core/src/main/java/stirling/software/SPDF/config/WAUTrackingFilter.java b/app/core/src/main/java/stirling/software/SPDF/config/WAUTrackingFilter.java
new file mode 100644
index 000000000..08362fa0b
--- /dev/null
+++ b/app/core/src/main/java/stirling/software/SPDF/config/WAUTrackingFilter.java
@@ -0,0 +1,49 @@
+package stirling.software.SPDF.config;
+
+import java.io.IOException;
+
+import jakarta.servlet.Filter;
+import jakarta.servlet.FilterChain;
+import jakarta.servlet.ServletException;
+import jakarta.servlet.ServletRequest;
+import jakarta.servlet.ServletResponse;
+import jakarta.servlet.http.HttpServletRequest;
+
+import org.springframework.boot.autoconfigure.condition.ConditionalOnProperty;
+import org.springframework.stereotype.Component;
+
+import lombok.RequiredArgsConstructor;
+import lombok.extern.slf4j.Slf4j;
+
+import stirling.software.SPDF.service.WeeklyActiveUsersService;
+
+/**
+ * Filter to track browser IDs for Weekly Active Users (WAU) counting.
+ * Only active when security is disabled (no-login mode).
+ */
+@Component
+@ConditionalOnProperty(name = "security.enableLogin", havingValue = "false")
+@RequiredArgsConstructor
+@Slf4j
+public class WAUTrackingFilter implements Filter {
+
+    private final WeeklyActiveUsersService wauService;
+
+    @Override
+    public void doFilter(ServletRequest request, ServletResponse response, FilterChain chain)
+            throws IOException, ServletException {
+
+        if (request instanceof HttpServletRequest httpRequest) {
+            // Extract browser ID from header
+            String browserId = httpRequest.getHeader("X-Browser-Id");
+
+            if (browserId != null && !browserId.trim().isEmpty()) {
+                // Record browser access
+                wauService.recordBrowserAccess(browserId);
+            }
+        }
+
+        // Continue the filter chain
+        chain.doFilter(request, response);
+    }
+}
diff --git a/app/core/src/main/java/stirling/software/SPDF/config/WebMvcConfig.java b/app/core/src/main/java/stirling/software/SPDF/config/WebMvcConfig.java
index 0823c29e9..fc578fdbc 100644
--- a/app/core/src/main/java/stirling/software/SPDF/config/WebMvcConfig.java
+++ b/app/core/src/main/java/stirling/software/SPDF/config/WebMvcConfig.java
@@ -46,8 +46,24 @@ public class WebMvcConfig implements WebMvcConfigurer {
                             "tauri://localhost",
                             "http://tauri.localhost",
                             "https://tauri.localhost")
-                    .allowedMethods("GET", "POST", "PUT", "DELETE", "OPTIONS", "PATCH")
-                    .allowedHeaders("*")
+                    .allowedMethods("GET", "POST", "PUT", "PATCH", "DELETE", "OPTIONS")
+                    .allowedHeaders(
+                            "Authorization",
+                            "Content-Type",
+                            "X-Requested-With",
+                            "Accept",
+                            "Origin",
+                            "X-API-KEY",
+                            "X-CSRF-TOKEN",
+                            "X-XSRF-TOKEN",
+                            "X-Browser-Id")
+                    .exposedHeaders(
+                            "WWW-Authenticate",
+                            "X-Total-Count",
+                            "X-Page-Number",
+                            "X-Page-Size",
+                            "Content-Disposition",
+                            "Content-Type")
                     .allowCredentials(true)
                     .maxAge(3600);
         } else if (hasConfiguredOrigins) {
@@ -63,13 +79,53 @@ public class WebMvcConfig implements WebMvcConfigurer {
                             .toArray(new String[0]);
 
             registry.addMapping("/**")
-                    .allowedOrigins(allowedOrigins)
-                    .allowedMethods("GET", "POST", "PUT", "DELETE", "OPTIONS", "PATCH")
-                    .allowedHeaders("*")
+                    .allowedOriginPatterns(allowedOrigins)
+                    .allowedMethods("GET", "POST", "PUT", "PATCH", "DELETE", "OPTIONS")
+                    .allowedHeaders(
+                            "Authorization",
+                            "Content-Type",
+                            "X-Requested-With",
+                            "Accept",
+                            "Origin",
+                            "X-API-KEY",
+                            "X-CSRF-TOKEN",
+                            "X-XSRF-TOKEN",
+                            "X-Browser-Id")
+                    .exposedHeaders(
+                            "WWW-Authenticate",
+                            "X-Total-Count",
+                            "X-Page-Number",
+                            "X-Page-Size",
+                            "Content-Disposition",
+                            "Content-Type")
+                    .allowCredentials(true)
+                    .maxAge(3600);
+        } else {
+            // Default to allowing all origins when nothing is configured
+            logger.info(
+                    "No CORS allowed origins configured in settings.yml (system.corsAllowedOrigins); allowing all origins.");
+            registry.addMapping("/**")
+                    .allowedOriginPatterns("*")
+                    .allowedMethods("GET", "POST", "PUT", "PATCH", "DELETE", "OPTIONS")
+                    .allowedHeaders(
+                            "Authorization",
+                            "Content-Type",
+                            "X-Requested-With",
+                            "Accept",
+                            "Origin",
+                            "X-API-KEY",
+                            "X-CSRF-TOKEN",
+                            "X-XSRF-TOKEN",
+                            "X-Browser-Id")
+                    .exposedHeaders(
+                            "WWW-Authenticate",
+                            "X-Total-Count",
+                            "X-Page-Number",
+                            "X-Page-Size",
+                            "Content-Disposition",
+                            "Content-Type")
                     .allowCredentials(true)
                     .maxAge(3600);
         }
-        // If no origins are configured and not in Tauri mode, CORS is not enabled (secure by
-        // default)
     }
 }
diff --git a/app/core/src/main/java/stirling/software/SPDF/controller/api/misc/ConfigController.java b/app/core/src/main/java/stirling/software/SPDF/controller/api/misc/ConfigController.java
index ffbec5a7d..a4a169cd9 100644
--- a/app/core/src/main/java/stirling/software/SPDF/controller/api/misc/ConfigController.java
+++ b/app/core/src/main/java/stirling/software/SPDF/controller/api/misc/ConfigController.java
@@ -154,6 +154,25 @@ public class ConfigController {
                 // EE features not available, continue without them
             }
 
+            // Add version and machine info for update checking
+            try {
+                if (applicationContext.containsBean("appVersion")) {
+                    configData.put(
+                            "appVersion", applicationContext.getBean("appVersion", String.class));
+                }
+                if (applicationContext.containsBean("machineType")) {
+                    configData.put(
+                            "machineType", applicationContext.getBean("machineType", String.class));
+                }
+                if (applicationContext.containsBean("activeSecurity")) {
+                    configData.put(
+                            "activeSecurity",
+                            applicationContext.getBean("activeSecurity", Boolean.class));
+                }
+            } catch (Exception e) {
+                // Version/machine info not available
+            }
+
             return ResponseEntity.ok(configData);
 
         } catch (Exception e) {
diff --git a/app/core/src/main/java/stirling/software/SPDF/controller/web/MetricsController.java b/app/core/src/main/java/stirling/software/SPDF/controller/web/MetricsController.java
index 8f17e0baf..53e60a6b5 100644
--- a/app/core/src/main/java/stirling/software/SPDF/controller/web/MetricsController.java
+++ b/app/core/src/main/java/stirling/software/SPDF/controller/web/MetricsController.java
@@ -23,6 +23,7 @@ import lombok.extern.slf4j.Slf4j;
 
 import stirling.software.SPDF.config.EndpointInspector;
 import stirling.software.SPDF.config.StartupApplicationListener;
+import stirling.software.SPDF.service.WeeklyActiveUsersService;
 import stirling.software.common.annotations.api.InfoApi;
 import stirling.software.common.model.ApplicationProperties;
 
@@ -34,6 +35,7 @@ public class MetricsController {
     private final ApplicationProperties applicationProperties;
     private final MeterRegistry meterRegistry;
     private final EndpointInspector endpointInspector;
+    private final Optional<WeeklyActiveUsersService> wauService;
     private boolean metricsEnabled;
 
     @PostConstruct
@@ -352,6 +354,35 @@ public class MetricsController {
         return ResponseEntity.ok(formatDuration(uptime));
     }
 
+    @GetMapping("/wau")
+    @Operation(
+            summary = "Weekly Active Users statistics",
+            description =
+                    "Returns WAU (Weekly Active Users) count and total unique browsers. "
+                            + "Only available when security is disabled (no-login mode). "
+                            + "Tracks unique browsers via client-generated UUID in localStorage.")
+    public ResponseEntity<?> getWeeklyActiveUsers() {
+        if (!metricsEnabled) {
+            return ResponseEntity.status(HttpStatus.FORBIDDEN).body("This endpoint is disabled.");
+        }
+
+        // Check if WAU service is available (only when security.enableLogin=false)
+        if (wauService.isEmpty()) {
+            return ResponseEntity.status(HttpStatus.NOT_FOUND)
+                    .body("WAU tracking is only available when security is disabled (no-login mode)");
+        }
+
+        WeeklyActiveUsersService service = wauService.get();
+
+        Map<String, Object> wauStats = new HashMap<>();
+        wauStats.put("weeklyActiveUsers", service.getWeeklyActiveUsers());
+        wauStats.put("totalUniqueBrowsers", service.getTotalUniqueBrowsers());
+        wauStats.put("daysOnline", service.getDaysOnline());
+        wauStats.put("trackingSince", service.getStartTime().toString());
+
+        return ResponseEntity.ok(wauStats);
+    }
+
     private String formatDuration(Duration duration) {
         long days = duration.toDays();
         long hours = duration.toHoursPart();
diff --git a/app/core/src/main/java/stirling/software/SPDF/service/WeeklyActiveUsersService.java b/app/core/src/main/java/stirling/software/SPDF/service/WeeklyActiveUsersService.java
new file mode 100644
index 000000000..ddf3a7b26
--- /dev/null
+++ b/app/core/src/main/java/stirling/software/SPDF/service/WeeklyActiveUsersService.java
@@ -0,0 +1,100 @@
+package stirling.software.SPDF.service;
+
+import java.time.Instant;
+import java.time.temporal.ChronoUnit;
+import java.util.Map;
+import java.util.concurrent.ConcurrentHashMap;
+
+import org.springframework.stereotype.Service;
+
+import lombok.extern.slf4j.Slf4j;
+
+/**
+ * Service for tracking Weekly Active Users (WAU) in no-login mode.
+ * Uses in-memory storage with automatic cleanup of old entries.
+ */
+@Service
+@Slf4j
+public class WeeklyActiveUsersService {
+
+    // Map of browser ID -> last seen timestamp
+    private final Map<String, Instant> activeBrowsers = new ConcurrentHashMap<>();
+
+    // Track total unique browsers seen (overall)
+    private long totalUniqueBrowsers = 0;
+
+    // Application start time
+    private final Instant startTime = Instant.now();
+
+    /**
+     * Records a browser access with the current timestamp
+     * @param browserId Unique browser identifier from X-Browser-Id header
+     */
+    public void recordBrowserAccess(String browserId) {
+        if (browserId == null || browserId.trim().isEmpty()) {
+            return;
+        }
+
+        boolean isNewBrowser = !activeBrowsers.containsKey(browserId);
+        activeBrowsers.put(browserId, Instant.now());
+
+        if (isNewBrowser) {
+            totalUniqueBrowsers++;
+            log.debug("New browser recorded: {} (Total: {})", browserId, totalUniqueBrowsers);
+        }
+    }
+
+    /**
+     * Gets the count of unique browsers seen in the last 7 days
+     * @return Weekly Active Users count
+     */
+    public long getWeeklyActiveUsers() {
+        cleanupOldEntries();
+        return activeBrowsers.size();
+    }
+
+    /**
+     * Gets the total count of unique browsers ever seen
+     * @return Total unique browsers count
+     */
+    public long getTotalUniqueBrowsers() {
+        return totalUniqueBrowsers;
+    }
+
+    /**
+     * Gets the number of days the service has been running
+     * @return Days online
+     */
+    public long getDaysOnline() {
+        return ChronoUnit.DAYS.between(startTime, Instant.now());
+    }
+
+    /**
+     * Gets the timestamp when tracking started
+     * @return Start time
+     */
+    public Instant getStartTime() {
+        return startTime;
+    }
+
+    /**
+     * Removes entries older than 7 days
+     */
+    private void cleanupOldEntries() {
+        Instant sevenDaysAgo = Instant.now().minus(7, ChronoUnit.DAYS);
+        activeBrowsers.entrySet().removeIf(entry -> entry.getValue().isBefore(sevenDaysAgo));
+    }
+
+    /**
+     * Manual cleanup trigger (can be called by scheduled task if needed)
+     */
+    public void performCleanup() {
+        int sizeBefore = activeBrowsers.size();
+        cleanupOldEntries();
+        int sizeAfter = activeBrowsers.size();
+
+        if (sizeBefore != sizeAfter) {
+            log.debug("Cleaned up {} old browser entries", sizeBefore - sizeAfter);
+        }
+    }
+}
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/ee/LicenseKeyChecker.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/ee/LicenseKeyChecker.java
index 212922d55..050a565c2 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/ee/LicenseKeyChecker.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/configuration/ee/LicenseKeyChecker.java
@@ -113,7 +113,12 @@ public class LicenseKeyChecker {
 
     public void updateLicenseKey(String newKey) throws IOException {
         applicationProperties.getPremium().setKey(newKey);
-        GeneralUtils.saveKeyToSettings("EnterpriseEdition.key", newKey);
+        GeneralUtils.saveKeyToSettings("premium.key", newKey);
+        evaluateLicense();
+        synchronizeLicenseSettings();
+    }
+
+    public void resyncLicense() {
         evaluateLicense();
         synchronizeLicenseSettings();
     }
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/controller/api/AdminLicenseController.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/controller/api/AdminLicenseController.java
new file mode 100644
index 000000000..7bd5836c8
--- /dev/null
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/controller/api/AdminLicenseController.java
@@ -0,0 +1,245 @@
+package stirling.software.proprietary.security.controller.api;
+
+import java.util.HashMap;
+import java.util.Map;
+
+import org.springframework.beans.factory.annotation.Autowired;
+import org.springframework.http.ResponseEntity;
+import org.springframework.security.access.prepost.PreAuthorize;
+import org.springframework.web.bind.annotation.GetMapping;
+import org.springframework.web.bind.annotation.PostMapping;
+import org.springframework.web.bind.annotation.RequestBody;
+import org.springframework.web.bind.annotation.RequestMapping;
+import org.springframework.web.bind.annotation.RestController;
+
+import io.swagger.v3.oas.annotations.Operation;
+import io.swagger.v3.oas.annotations.tags.Tag;
+
+import lombok.extern.slf4j.Slf4j;
+
+import stirling.software.common.model.ApplicationProperties;
+import stirling.software.common.util.GeneralUtils;
+import stirling.software.proprietary.security.configuration.ee.KeygenLicenseVerifier;
+import stirling.software.proprietary.security.configuration.ee.KeygenLicenseVerifier.License;
+import stirling.software.proprietary.security.configuration.ee.LicenseKeyChecker;
+
+/**
+ * Admin controller for license management. Provides installation ID for Stripe checkout metadata
+ * and endpoints for managing license keys.
+ */
+@RestController
+@Slf4j
+@RequestMapping("/api/v1/admin")
+@PreAuthorize("hasRole('ROLE_ADMIN')")
+@Tag(name = "Admin License Management", description = "Admin-only License Management APIs")
+public class AdminLicenseController {
+
+    @Autowired(required = false)
+    private LicenseKeyChecker licenseKeyChecker;
+
+    @Autowired(required = false)
+    private KeygenLicenseVerifier keygenLicenseVerifier;
+
+    @Autowired private ApplicationProperties applicationProperties;
+
+    /**
+     * Get the installation ID (machine fingerprint) for this self-hosted instance. This ID is used
+     * as metadata in Stripe checkout to link licenses to specific installations.
+     *
+     * @return Map containing the installation ID
+     */
+    @GetMapping("/installation-id")
+    @Operation(
+            summary = "Get installation ID",
+            description =
+                    "Returns the unique installation ID (MAC-based fingerprint) for this"
+                            + " self-hosted instance")
+    public ResponseEntity<Map<String, String>> getInstallationId() {
+        try {
+            String installationId = GeneralUtils.generateMachineFingerprint();
+            log.info("Admin requested installation ID: {}", installationId);
+            return ResponseEntity.ok(Map.of("installationId", installationId));
+        } catch (Exception e) {
+            log.error("Failed to generate installation ID", e);
+            return ResponseEntity.internalServerError()
+                    .body(Map.of("error", "Failed to generate installation ID"));
+        }
+    }
+
+    /**
+     * Save and activate a license key. This endpoint accepts a license key from the frontend (e.g.,
+     * after Stripe checkout) and activates it on the backend.
+     *
+     * @param request Map containing the license key
+     * @return Response with success status, license type, and whether restart is required
+     */
+    @PostMapping("/license-key")
+    @Operation(
+            summary = "Save and activate license key",
+            description =
+                    "Accepts a license key and activates it on the backend. Returns the activated"
+                            + " license type.")
+    public ResponseEntity<Map<String, Object>> saveLicenseKey(
+            @RequestBody Map<String, String> request) {
+        String licenseKey = request.get("licenseKey");
+
+        // Reject null but allow empty string to clear license
+        if (licenseKey == null) {
+            return ResponseEntity.badRequest()
+                    .body(Map.of("success", false, "error", "License key is required"));
+        }
+
+        try {
+            if (licenseKeyChecker == null) {
+                return ResponseEntity.internalServerError()
+                        .body(Map.of("success", false, "error", "License checker not available"));
+            }
+            // assume premium enabled when setting license key
+            applicationProperties.getPremium().setEnabled(true);
+
+            // Use existing LicenseKeyChecker to update and validate license
+            // Empty string will be evaluated as NORMAL license (free tier)
+            licenseKeyChecker.updateLicenseKey(licenseKey.trim());
+
+            // Get current license status
+            License license = licenseKeyChecker.getPremiumLicenseEnabledResult();
+
+            // Auto-enable premium features if license is valid
+            if (license != License.NORMAL) {
+                GeneralUtils.saveKeyToSettings("premium.enabled", true);
+                // Enable premium features
+
+                // Save maxUsers from license metadata
+                Integer maxUsers = applicationProperties.getPremium().getMaxUsers();
+                if (maxUsers != null) {
+                    GeneralUtils.saveKeyToSettings("premium.maxUsers", maxUsers);
+                }
+            } else {
+                GeneralUtils.saveKeyToSettings("premium.enabled", false);
+                log.info("License key is not valid for premium features: type={}", license.name());
+            }
+
+            Map<String, Object> response = new HashMap<>();
+            response.put("success", true);
+            response.put("licenseType", license.name());
+            response.put("enabled", applicationProperties.getPremium().isEnabled());
+            response.put("maxUsers", applicationProperties.getPremium().getMaxUsers());
+            response.put("requiresRestart", false); // Dynamic evaluation works
+            response.put("message", "License key saved and activated");
+
+            log.info("License key saved and activated: type={}", license.name());
+
+            return ResponseEntity.ok(response);
+        } catch (Exception e) {
+            log.error("Failed to save license key", e);
+            return ResponseEntity.badRequest()
+                    .body(
+                            Map.of(
+                                    "success",
+                                    false,
+                                    "error",
+                                    "Failed to activate license: " + e.getMessage()));
+        }
+    }
+
+    /**
+     * Resync the current license with Keygen. This endpoint re-validates the existing license key
+     * and updates the max users setting. Used after subscription upgrades to sync the new license
+     * limits.
+     *
+     * @return Response with updated license information
+     */
+    @PostMapping("/license/resync")
+    @Operation(
+            summary = "Resync license with Keygen",
+            description =
+                    "Re-validates the existing license key with Keygen and updates local settings."
+                            + " Used after subscription upgrades.")
+    public ResponseEntity<Map<String, Object>> resyncLicense() {
+        try {
+            if (licenseKeyChecker == null) {
+                return ResponseEntity.internalServerError()
+                        .body(Map.of("success", false, "error", "License checker not available"));
+            }
+
+            String currentKey = applicationProperties.getPremium().getKey();
+            if (currentKey == null || currentKey.trim().isEmpty()) {
+                return ResponseEntity.badRequest()
+                        .body(Map.of("success", false, "error", "No license key configured"));
+            }
+
+            log.info("Resyncing license with Keygen");
+
+            // Re-validate license and sync settings
+            licenseKeyChecker.resyncLicense();
+
+            // Get updated license status
+            License license = licenseKeyChecker.getPremiumLicenseEnabledResult();
+            ApplicationProperties.Premium premium = applicationProperties.getPremium();
+
+            Map<String, Object> response = new HashMap<>();
+            response.put("success", true);
+            response.put("licenseType", license.name());
+            response.put("enabled", premium.isEnabled());
+            response.put("maxUsers", premium.getMaxUsers());
+            response.put("message", "License resynced successfully");
+
+            log.info(
+                    "License resynced: type={}, maxUsers={}",
+                    license.name(),
+                    premium.getMaxUsers());
+
+            return ResponseEntity.ok(response);
+        } catch (Exception e) {
+            log.error("Failed to resync license", e);
+            return ResponseEntity.internalServerError()
+                    .body(
+                            Map.of(
+                                    "success",
+                                    false,
+                                    "error",
+                                    "Failed to resync license: " + e.getMessage()));
+        }
+    }
+
+    /**
+     * Get information about the current license key status, including license type, enabled status,
+     * and max users.
+     *
+     * @return Map containing license information
+     */
+    @GetMapping("/license-info")
+    @Operation(
+            summary = "Get license information",
+            description =
+                    "Returns information about the current license including type, enabled status,"
+                            + " and max users")
+    public ResponseEntity<Map<String, Object>> getLicenseInfo() {
+        try {
+            Map<String, Object> response = new HashMap<>();
+
+            if (licenseKeyChecker != null) {
+                License license = licenseKeyChecker.getPremiumLicenseEnabledResult();
+                response.put("licenseType", license.name());
+            } else {
+                response.put("licenseType", License.NORMAL.name());
+            }
+
+            ApplicationProperties.Premium premium = applicationProperties.getPremium();
+            response.put("enabled", premium.isEnabled());
+            response.put("maxUsers", premium.getMaxUsers());
+            response.put("hasKey", premium.getKey() != null && !premium.getKey().trim().isEmpty());
+
+            // Include license key for upgrades (admin-only endpoint)
+            if (premium.getKey() != null && !premium.getKey().trim().isEmpty()) {
+                response.put("licenseKey", premium.getKey());
+            }
+
+            return ResponseEntity.ok(response);
+        } catch (Exception e) {
+            log.error("Failed to get license info", e);
+            return ResponseEntity.internalServerError()
+                    .body(Map.of("error", "Failed to retrieve license information"));
+        }
+    }
+}
diff --git a/app/proprietary/src/main/java/stirling/software/proprietary/security/controller/api/AdminSettingsController.java b/app/proprietary/src/main/java/stirling/software/proprietary/security/controller/api/AdminSettingsController.java
index 27c924ae4..a4bdd9da5 100644
--- a/app/proprietary/src/main/java/stirling/software/proprietary/security/controller/api/AdminSettingsController.java
+++ b/app/proprietary/src/main/java/stirling/software/proprietary/security/controller/api/AdminSettingsController.java
@@ -299,6 +299,16 @@ public class AdminSettingsController {
                                         + String.join(", ", VALID_SECTION_NAMES));
             }
 
+            // Auto-enable premium features if license key is provided
+            if ("premium".equalsIgnoreCase(sectionName) && sectionData.containsKey("key")) {
+                Object keyValue = sectionData.get("key");
+                if (keyValue != null && !keyValue.toString().trim().isEmpty()) {
+                    // Automatically set enabled to true when a key is provided
+                    sectionData.put("enabled", true);
+                    log.info("Auto-enabling premium features because license key was provided");
+                }
+            }
+
             int updatedCount = 0;
             for (Map.Entry<String, Object> entry : sectionData.entrySet()) {
                 String propertyKey = entry.getKey();
diff --git a/frontend/package-lock.json b/frontend/package-lock.json
index 498218e70..84af9b0c8 100644
--- a/frontend/package-lock.json
+++ b/frontend/package-lock.json
@@ -39,10 +39,14 @@
         "@mui/icons-material": "^7.3.2",
         "@mui/material": "^7.3.2",
         "@reactour/tour": "^3.8.0",
+        "@stripe/react-stripe-js": "^4.0.2",
+        "@stripe/stripe-js": "^7.9.0",
+        "@supabase/supabase-js": "^2.47.13",
         "@tailwindcss/postcss": "^4.1.13",
         "@tanstack/react-virtual": "^3.13.12",
         "@tauri-apps/api": "^2.5.0",
         "@tauri-apps/plugin-fs": "^2.4.0",
+        "@tauri-apps/plugin-http": "^2.5.4",
         "autoprefixer": "^10.4.21",
         "axios": "^1.12.2",
         "globals": "^16.4.0",
@@ -3121,6 +3125,138 @@
         "url": "https://github.com/sindresorhus/is?sponsor=1"
       }
     },
+    "node_modules/@stripe/react-stripe-js": {
+      "version": "4.0.2",
+      "resolved": "https://registry.npmjs.org/@stripe/react-stripe-js/-/react-stripe-js-4.0.2.tgz",
+      "integrity": "sha512-l2wau+8/LOlHl+Sz8wQ1oDuLJvyw51nQCsu6/ljT6smqzTszcMHifjAJoXlnMfcou3+jK/kQyVe04u/ufyTXgg==",
+      "license": "MIT",
+      "dependencies": {
+        "prop-types": "^15.7.2"
+      },
+      "peerDependencies": {
+        "@stripe/stripe-js": ">=1.44.1 <8.0.0",
+        "react": ">=16.8.0 <20.0.0",
+        "react-dom": ">=16.8.0 <20.0.0"
+      }
+    },
+    "node_modules/@stripe/stripe-js": {
+      "version": "7.9.0",
+      "resolved": "https://registry.npmjs.org/@stripe/stripe-js/-/stripe-js-7.9.0.tgz",
+      "integrity": "sha512-ggs5k+/0FUJcIgNY08aZTqpBTtbExkJMYMLSMwyucrhtWexVOEY1KJmhBsxf+E/Q15f5rbwBpj+t0t2AW2oCsQ==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=12.16"
+      }
+    },
+    "node_modules/@supabase/auth-js": {
+      "version": "2.81.1",
+      "resolved": "https://registry.npmjs.org/@supabase/auth-js/-/auth-js-2.81.1.tgz",
+      "integrity": "sha512-K20GgiSm9XeRLypxYHa5UCnybWc2K0ok0HLbqCej/wRxDpJxToXNOwKt0l7nO8xI1CyQ+GrNfU6bcRzvdbeopQ==",
+      "license": "MIT",
+      "dependencies": {
+        "tslib": "2.8.1"
+      },
+      "engines": {
+        "node": ">=20.0.0"
+      }
+    },
+    "node_modules/@supabase/auth-js/node_modules/tslib": {
+      "version": "2.8.1",
+      "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.8.1.tgz",
+      "integrity": "sha512-oJFu94HQb+KVduSUQL7wnpmqnfmLsOA/nAh6b6EH0wCEoK0/mPeXU6c3wKDV83MkOuHPRHtSXKKU99IBazS/2w==",
+      "license": "0BSD"
+    },
+    "node_modules/@supabase/functions-js": {
+      "version": "2.81.1",
+      "resolved": "https://registry.npmjs.org/@supabase/functions-js/-/functions-js-2.81.1.tgz",
+      "integrity": "sha512-sYgSO3mlgL0NvBFS3oRfCK4OgKGQwuOWJLzfPyWg0k8MSxSFSDeN/JtrDJD5GQrxskP6c58+vUzruBJQY78AqQ==",
+      "license": "MIT",
+      "dependencies": {
+        "tslib": "2.8.1"
+      },
+      "engines": {
+        "node": ">=20.0.0"
+      }
+    },
+    "node_modules/@supabase/functions-js/node_modules/tslib": {
+      "version": "2.8.1",
+      "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.8.1.tgz",
+      "integrity": "sha512-oJFu94HQb+KVduSUQL7wnpmqnfmLsOA/nAh6b6EH0wCEoK0/mPeXU6c3wKDV83MkOuHPRHtSXKKU99IBazS/2w==",
+      "license": "0BSD"
+    },
+    "node_modules/@supabase/postgrest-js": {
+      "version": "2.81.1",
+      "resolved": "https://registry.npmjs.org/@supabase/postgrest-js/-/postgrest-js-2.81.1.tgz",
+      "integrity": "sha512-DePpUTAPXJyBurQ4IH2e42DWoA+/Qmr5mbgY4B6ZcxVc/ZUKfTVK31BYIFBATMApWraFc8Q/Sg+yxtfJ3E0wSg==",
+      "license": "MIT",
+      "dependencies": {
+        "tslib": "2.8.1"
+      },
+      "engines": {
+        "node": ">=20.0.0"
+      }
+    },
+    "node_modules/@supabase/postgrest-js/node_modules/tslib": {
+      "version": "2.8.1",
+      "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.8.1.tgz",
+      "integrity": "sha512-oJFu94HQb+KVduSUQL7wnpmqnfmLsOA/nAh6b6EH0wCEoK0/mPeXU6c3wKDV83MkOuHPRHtSXKKU99IBazS/2w==",
+      "license": "0BSD"
+    },
+    "node_modules/@supabase/realtime-js": {
+      "version": "2.81.1",
+      "resolved": "https://registry.npmjs.org/@supabase/realtime-js/-/realtime-js-2.81.1.tgz",
+      "integrity": "sha512-ViQ+Kxm8BuUP/TcYmH9tViqYKGSD1LBjdqx2p5J+47RES6c+0QHedM0PPAjthMdAHWyb2LGATE9PD2++2rO/tw==",
+      "license": "MIT",
+      "dependencies": {
+        "@types/phoenix": "^1.6.6",
+        "@types/ws": "^8.18.1",
+        "tslib": "2.8.1",
+        "ws": "^8.18.2"
+      },
+      "engines": {
+        "node": ">=20.0.0"
+      }
+    },
+    "node_modules/@supabase/realtime-js/node_modules/tslib": {
+      "version": "2.8.1",
+      "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.8.1.tgz",
+      "integrity": "sha512-oJFu94HQb+KVduSUQL7wnpmqnfmLsOA/nAh6b6EH0wCEoK0/mPeXU6c3wKDV83MkOuHPRHtSXKKU99IBazS/2w==",
+      "license": "0BSD"
+    },
+    "node_modules/@supabase/storage-js": {
+      "version": "2.81.1",
+      "resolved": "https://registry.npmjs.org/@supabase/storage-js/-/storage-js-2.81.1.tgz",
+      "integrity": "sha512-UNmYtjnZnhouqnbEMC1D5YJot7y0rIaZx7FG2Fv8S3hhNjcGVvO+h9We/tggi273BFkiahQPS/uRsapo1cSapw==",
+      "license": "MIT",
+      "dependencies": {
+        "tslib": "2.8.1"
+      },
+      "engines": {
+        "node": ">=20.0.0"
+      }
+    },
+    "node_modules/@supabase/storage-js/node_modules/tslib": {
+      "version": "2.8.1",
+      "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.8.1.tgz",
+      "integrity": "sha512-oJFu94HQb+KVduSUQL7wnpmqnfmLsOA/nAh6b6EH0wCEoK0/mPeXU6c3wKDV83MkOuHPRHtSXKKU99IBazS/2w==",
+      "license": "0BSD"
+    },
+    "node_modules/@supabase/supabase-js": {
+      "version": "2.81.1",
+      "resolved": "https://registry.npmjs.org/@supabase/supabase-js/-/supabase-js-2.81.1.tgz",
+      "integrity": "sha512-KSdY7xb2L0DlLmlYzIOghdw/na4gsMcqJ8u4sD6tOQJr+x3hLujU9s4R8N3ob84/1bkvpvlU5PYKa1ae+OICnw==",
+      "license": "MIT",
+      "dependencies": {
+        "@supabase/auth-js": "2.81.1",
+        "@supabase/functions-js": "2.81.1",
+        "@supabase/postgrest-js": "2.81.1",
+        "@supabase/realtime-js": "2.81.1",
+        "@supabase/storage-js": "2.81.1"
+      },
+      "engines": {
+        "node": ">=20.0.0"
+      }
+    },
     "node_modules/@sveltejs/acorn-typescript": {
       "version": "1.0.6",
       "resolved": "https://registry.npmjs.org/@sveltejs/acorn-typescript/-/acorn-typescript-1.0.6.tgz",
@@ -3888,6 +4024,15 @@
         "@tauri-apps/api": "^2.8.0"
       }
     },
+    "node_modules/@tauri-apps/plugin-http": {
+      "version": "2.5.4",
+      "resolved": "https://registry.npmjs.org/@tauri-apps/plugin-http/-/plugin-http-2.5.4.tgz",
+      "integrity": "sha512-/i4U/9za3mrytTgfRn5RHneKubZE/dwRmshYwyMvNRlkWjvu1m4Ma72kcbVJMZFGXpkbl+qLyWMGrihtWB76Zg==",
+      "license": "MIT OR Apache-2.0",
+      "dependencies": {
+        "@tauri-apps/api": "^2.8.0"
+      }
+    },
     "node_modules/@testing-library/dom": {
       "version": "10.4.1",
       "resolved": "https://registry.npmjs.org/@testing-library/dom/-/dom-10.4.1.tgz",
@@ -4194,7 +4339,6 @@
       "version": "24.9.1",
       "resolved": "https://registry.npmjs.org/@types/node/-/node-24.9.1.tgz",
       "integrity": "sha512-QoiaXANRkSXK6p0Duvt56W208du4P9Uye9hWLWgGMDTEoKPhuenzNcC4vGUmrNkiOKTlIrBoyNQYNpSwfEZXSg==",
-      "dev": true,
       "license": "MIT",
       "dependencies": {
         "undici-types": "~7.16.0"
@@ -4206,6 +4350,12 @@
       "integrity": "sha512-dISoDXWWQwUquiKsyZ4Ng+HX2KsPL7LyHKHQwgGFEA3IaKac4Obd+h2a/a6waisAoepJlBcx9paWqjA8/HVjCw==",
       "license": "MIT"
     },
+    "node_modules/@types/phoenix": {
+      "version": "1.6.6",
+      "resolved": "https://registry.npmjs.org/@types/phoenix/-/phoenix-1.6.6.tgz",
+      "integrity": "sha512-PIzZZlEppgrpoT2QgbnDU+MMzuR6BbCjllj0bM70lWoejMeNJAxCchxnv7J3XFkI8MpygtRpzXrIlmWUBclP5A==",
+      "license": "MIT"
+    },
     "node_modules/@types/prop-types": {
       "version": "15.7.15",
       "resolved": "https://registry.npmjs.org/@types/prop-types/-/prop-types-15.7.15.tgz",
@@ -4240,6 +4390,15 @@
         "@types/react": "*"
       }
     },
+    "node_modules/@types/ws": {
+      "version": "8.18.1",
+      "resolved": "https://registry.npmjs.org/@types/ws/-/ws-8.18.1.tgz",
+      "integrity": "sha512-ThVF6DCVhA8kUGy+aazFQ4kXQ7E1Ty7A3ypFOe0IcJV8O/M511G99AW24irKrW56Wt44yG9+ij8FaqoBGkuBXg==",
+      "license": "MIT",
+      "dependencies": {
+        "@types/node": "*"
+      }
+    },
     "node_modules/@types/yauzl": {
       "version": "2.10.3",
       "resolved": "https://registry.npmjs.org/@types/yauzl/-/yauzl-2.10.3.tgz",
@@ -14007,7 +14166,6 @@
       "version": "7.16.0",
       "resolved": "https://registry.npmjs.org/undici-types/-/undici-types-7.16.0.tgz",
       "integrity": "sha512-Zz+aZWSj8LE6zoxD+xrjh4VfkIG8Ya6LvYkZqtUQGJPZjYl53ypCaUwWqo7eI0x66KBGeRo+mlBEkMSeSZ38Nw==",
-      "dev": true,
       "license": "MIT"
     },
     "node_modules/universalify": {
@@ -14878,7 +15036,6 @@
       "version": "8.18.3",
       "resolved": "https://registry.npmjs.org/ws/-/ws-8.18.3.tgz",
       "integrity": "sha512-PEIGCY5tSlUt50cqyMXfCzX+oOPqN0vuGqWzbcJ2xvnkzkq46oOpz7dQaTDBdfICb4N14+GARUDw2XV2N4tvzg==",
-      "dev": true,
       "license": "MIT",
       "engines": {
         "node": ">=10.0.0"
diff --git a/frontend/package.json b/frontend/package.json
index 9d021a728..e4eae5b1c 100644
--- a/frontend/package.json
+++ b/frontend/package.json
@@ -26,19 +26,23 @@
     "@embedpdf/plugin-viewport": "^1.4.1",
     "@embedpdf/plugin-zoom": "^1.4.1",
     "@emotion/react": "^11.14.0",
-    "@tauri-apps/api": "^2.5.0",
-    "@tauri-apps/plugin-fs": "^2.4.0",
     "@emotion/styled": "^11.14.1",
     "@iconify/react": "^6.0.2",
     "@mantine/core": "^8.3.1",
     "@mantine/dates": "^8.3.1",
     "@mantine/dropzone": "^8.3.1",
     "@mantine/hooks": "^8.3.1",
+    "@stripe/react-stripe-js": "^4.0.2",
+    "@stripe/stripe-js": "^7.9.0",
+    "@supabase/supabase-js": "^2.47.13",
     "@mui/icons-material": "^7.3.2",
     "@mui/material": "^7.3.2",
     "@reactour/tour": "^3.8.0",
     "@tailwindcss/postcss": "^4.1.13",
     "@tanstack/react-virtual": "^3.13.12",
+    "@tauri-apps/api": "^2.5.0",
+    "@tauri-apps/plugin-fs": "^2.4.0",
+    "@tauri-apps/plugin-http": "^2.5.4",
     "autoprefixer": "^10.4.21",
     "axios": "^1.12.2",
     "globals": "^16.4.0",
@@ -111,11 +115,11 @@
     ]
   },
   "devDependencies": {
-    "@tauri-apps/cli": "^2.5.0",
     "@eslint/js": "^9.36.0",
     "@iconify-json/material-symbols": "^1.2.37",
     "@iconify/utils": "^3.0.2",
     "@playwright/test": "^1.55.0",
+    "@tauri-apps/cli": "^2.5.0",
     "@testing-library/dom": "^10.4.1",
     "@testing-library/jest-dom": "^6.8.0",
     "@testing-library/react": "^16.3.0",
diff --git a/frontend/public/locales/en-GB/translation.json b/frontend/public/locales/en-GB/translation.json
index c6747c0de..8a04d3d19 100644
--- a/frontend/public/locales/en-GB/translation.json
+++ b/frontend/public/locales/en-GB/translation.json
@@ -359,7 +359,15 @@
       "defaultPdfEditorInactive": "Another application is set as default",
       "defaultPdfEditorChecking": "Checking...",
       "defaultPdfEditorSet": "Already Default",
-      "setAsDefault": "Set as Default"
+      "setAsDefault": "Set as Default",
+      "updates": {
+        "title": "Software Updates",
+        "description": "Check for updates and view version information",
+        "currentVersion": "Current Version",
+        "latestVersion": "Latest Version",
+        "checkForUpdates": "Check for Updates",
+        "viewDetails": "View Details"
+      }
     },
     "hotkeys": {
       "title": "Keyboard Shortcuts",
@@ -380,6 +388,37 @@
       "searchPlaceholder": "Search tools..."
     }
   },
+  "update": {
+    "modalTitle": "Update Available",
+    "current": "Current Version",
+    "latest": "Latest Version",
+    "latestStable": "Latest Stable",
+    "priorityLabel": "Priority",
+    "recommendedAction": "Recommended Action",
+    "breakingChangesDetected": "Breaking Changes Detected",
+    "breakingChangesMessage": "Some versions contain breaking changes. Please review the migration guides below before updating.",
+    "migrationGuides": "Migration Guides",
+    "viewGuide": "View Guide",
+    "loadingDetailedInfo": "Loading detailed information...",
+    "close": "Close",
+    "viewAllReleases": "View All Releases",
+    "downloadLatest": "Download Latest",
+    "availableUpdates": "Available Updates",
+    "unableToLoadDetails": "Unable to load detailed information.",
+    "version": "Version",
+    "urgentUpdateAvailable": "Urgent Update",
+    "updateAvailable": "Update Available",
+    "releaseNotes": "Release Notes",
+    "priority": {
+      "urgent": "Urgent",
+      "normal": "Normal",
+      "minor": "Minor",
+      "low": "Low"
+    },
+    "breakingChanges": "Breaking Changes",
+    "breakingChangesDefault": "This version contains breaking changes.",
+    "migrationGuide": "Migration Guide"
+  },
   "changeCreds": {
     "title": "Change Credentials",
     "header": "Update Your Account Details",
@@ -2092,13 +2131,54 @@
       "title": "Draw your signature",
       "clear": "Clear"
     },
+    "canvas": {
+      "heading": "Draw your signature",
+      "clickToOpen": "Click to open the drawing canvas",
+      "modalTitle": "Draw your signature",
+      "colorLabel": "Colour",
+      "penSizeLabel": "Pen size",
+      "penSizePlaceholder": "Size",
+      "clear": "Clear canvas",
+      "colorPickerTitle": "Choose stroke colour"
+    },
     "text": {
       "name": "Signer Name",
-      "placeholder": "Enter your full name"
+      "placeholder": "Enter your full name",
+      "fontLabel": "Font",
+      "fontSizeLabel": "Font size",
+      "fontSizePlaceholder": "Type or select font size (8-200)",
+      "colorLabel": "Text colour"
     },
     "clear": "Clear",
     "add": "Add",
-    "saved": "Saved Signatures",
+    "saved": {
+      "heading": "Saved signatures",
+      "description": "Reuse saved signatures at any time.",
+      "emptyTitle": "No saved signatures yet",
+      "emptyDescription": "Draw, upload, or type a signature above, then use \"Save to library\" to keep up to {{max}} favourites ready to use.",
+      "type": {
+        "canvas": "Drawing",
+        "image": "Upload",
+        "text": "Text"
+      },
+      "limitTitle": "Limit reached",
+      "limitDescription": "Remove a saved signature before adding new ones (max {{max}}).",
+      "carouselPosition": "{{current}} of {{total}}",
+      "prev": "Previous",
+      "next": "Next",
+      "delete": "Remove",
+      "label": "Label",
+      "defaultLabel": "Signature",
+      "defaultCanvasLabel": "Drawing signature",
+      "defaultImageLabel": "Uploaded signature",
+      "defaultTextLabel": "Typed signature",
+      "saveButton": "Save signature",
+      "saveUnavailable": "Create a signature first to save it.",
+      "noChanges": "Current signature is already saved.",
+      "status": {
+        "saved": "Saved"
+      }
+    },
     "save": "Save Signature",
     "applySignatures": "Apply Signatures",
     "personalSigs": "Personal Signatures",
@@ -2117,12 +2197,18 @@
     "steps": {
       "configure": "Configure Signature"
     },
+    "step": {
+      "createDesc": "Choose how you want to create the signature",
+      "place": "Place & save",
+      "placeDesc": "Position the signature on your PDF"
+    },
     "type": {
       "title": "Signature Type",
       "draw": "Draw",
       "canvas": "Canvas",
       "image": "Image",
-      "text": "Text"
+      "text": "Text",
+      "saved": "Saved"
     },
     "image": {
       "label": "Upload signature image",
@@ -2133,11 +2219,17 @@
       "title": "How to add signature",
       "canvas": "After drawing your signature in the canvas, close the modal then click anywhere on the PDF to place it.",
       "image": "After uploading your signature image above, click anywhere on the PDF to place it.",
-      "text": "After entering your name above, click anywhere on the PDF to place your signature."
+      "saved": "Select a saved signature above, then click anywhere on the PDF to place it.",
+      "text": "After entering your name above, click anywhere on the PDF to place your signature.",
+      "paused": "Placement paused",
+      "resumeHint": "Resume placement to click and add your signature.",
+      "noSignature": "Create a signature above to enable placement tools."
     },
     "mode": {
       "move": "Move Signature",
-      "place": "Place Signature"
+      "place": "Place Signature",
+      "pause": "Pause placement",
+      "resume": "Resume placement"
     },
     "updateAndPlace": "Update and Place",
     "activate": "Activate Signature Placement",
@@ -2283,15 +2375,78 @@
     "tags": "differentiate,contrast,changes,analysis",
     "title": "Compare",
     "header": "Compare PDFs",
-    "highlightColor": {
-      "1": "Highlight Colour 1:",
-      "2": "Highlight Colour 2:"
+    "clearSelected": "Clear selected",
+    "clear": {
+      "confirmTitle": "Clear selected PDFs?",
+      "confirmBody": "This will close the current comparison and take you back to Active Files.",
+      "confirm": "Clear and return"
+    },
+    "review": {
+      "title": "Comparison Result",
+      "actionsHint": "Review the comparison, switch document roles, or export the summary.",
+      "switchOrder": "Switch order",
+      "exportSummary": "Export summary"
+    },
+    "base": {
+      "label": "Original document",
+      "placeholder": "Select the original PDF"
+    },
+    "comparison": {
+      "label": "Edited document",
+      "placeholder": "Select the edited PDF"
+    },
+    "addFilesHint": "Add PDFs in the Files step to enable selection.",
+    "noFiles": "No PDFs available yet",
+    "pages": "Pages",
+    "selection": {
+      "originalEditedTitle": "Select Original and Edited PDFs"
+    },
+    "original": { "label": "Original PDF" },
+    "edited": { "label": "Edited PDF" },
+    "swap": {
+      "confirmTitle": "Re-run comparison?",
+      "confirmBody": "This will rerun the tool. Are you sure you want to swap the order of Original and Edited?",
+      "confirm": "Swap and Re-run"
+    },
+    "cta": "Compare",
+    "loading": "Comparing...",
+
+    "summary": {
+      "baseHeading": "Original document",
+      "comparisonHeading": "Edited document",
+      "pageLabel": "Page"
+    },
+    "rendering": {
+      "pageNotReadyTitle": "Page not rendered yet",
+      "pageNotReadyBody": "Some pages are still rendering. Navigation will snap once they are ready.",
+      "rendering": "rendering",
+      "inProgress": "At least one of these PDFs are very large, scrolling won't be smooth until the rendering is complete",
+      "pagesRendered": "pages rendered",
+      "complete": "Page rendering complete"
+    },
+    "dropdown": {
+      "deletionsLabel": "Deletions",
+      "additionsLabel": "Additions",
+      "deletions": "Deletions ({{count}})",
+      "additions": "Additions ({{count}})",
+      "searchPlaceholder": "Search changes...",
+      "noResults": "No changes found"
     },
     "document": {
       "1": "Document 1",
       "2": "Document 2"
     },
-    "submit": "Compare",
+    "longJob": {
+      "title": "Large comparison in progress",
+      "body": "These PDFs together exceed 2,000 pages. Processing can take several minutes."
+    },
+    "slowOperation": {
+      "title": "Still working…",
+      "body": "This comparison is taking longer than usual. You can let it continue or cancel it.",
+      "cancel": "Cancel comparison"
+    },
+
+    "newLine": "new-line",
     "complex": {
       "message": "One or both of the provided documents are large files, accuracy of comparison may be reduced"
     },
@@ -4046,10 +4201,26 @@
         "title": "Premium & Enterprise",
         "description": "Configure your premium or enterprise license key.",
         "license": "License Configuration",
-        "key": "License Key",
-        "key.description": "Enter your premium or enterprise license key",
-        "enabled": "Enable Premium Features",
-        "enabled.description": "Enable license key checks for pro/enterprise features",
+        "licenseKey": {
+          "toggle": "Got a license key or certificate file?",
+          "info": "If you have a license key or certificate file from a direct purchase, you can enter it here to activate premium or enterprise features."
+        },
+        "key": {
+          "label": "License Key",
+          "description": "Enter your premium or enterprise license key. Premium features will be automatically enabled when a key is provided.",
+          "success": "License Key Saved",
+          "successMessage": "Your license key has been activated successfully. No restart required.",
+          "overwriteWarning": {
+            "title": "⚠️ Warning: Existing License Detected",
+            "line1": "Overwriting your current license key cannot be undone.",
+            "line2": "Your previous license will be permanently lost unless you have backed it up elsewhere.",
+            "line3": "Important: Keep license keys private and secure. Never share them publicly."
+          }
+        },
+        "enabled": {
+          "label": "Enable Premium Features",
+          "description": "Enable license key checks for pro/enterprise features"
+        },
         "movedFeatures": {
           "title": "Premium Features Distributed",
           "message": "Premium and Enterprise features are now organized in their respective sections:"
@@ -4426,6 +4597,9 @@
       "processImagesDesc": "Converts multiple image files into a single PDF document, then applies OCR technology to extract searchable text from the images."
     }
   },
+  "colorPicker": {
+    "title": "Choose colour"
+  },
   "common": {
     "copy": "Copy",
     "copied": "Copied!",
@@ -4435,7 +4609,12 @@
     "used": "used",
     "available": "available",
     "cancel": "Cancel",
-    "preview": "Preview"
+    "preview": "Preview",
+    "close": "Close",
+    "done": "Done",
+    "loading": "Loading...",
+    "back": "Back",
+    "continue": "Continue"
   },
   "config": {
     "overview": {
@@ -5035,6 +5214,14 @@
     "showComparison": "Compare All Features",
     "hideComparison": "Hide Feature Comparison",
     "featureComparison": "Feature Comparison",
+    "from": "From",
+    "perMonth": "/month",
+    "licensedSeats": "Licensed: {{count}} seats",
+    "includedInCurrent": "Included in Your Plan",
+    "selectPlan": "Select Plan",
+    "manageSubscription": {
+      "description": "Manage your subscription, billing, and payment methods"
+    },
     "activePlan": {
       "title": "Active Plan",
       "subtitle": "Your current subscription details"
@@ -5052,13 +5239,16 @@
       "upTo": "Up to"
     },
     "period": {
-      "month": "month"
+      "month": "month",
+      "perUserPerMonth": "/user/month"
     },
     "free": {
       "name": "Free",
       "highlight1": "Limited Tool Usage Per week",
       "highlight2": "Access to all tools",
-      "highlight3": "Community support"
+      "highlight3": "Community support",
+      "forever": "Forever free",
+      "included": "Included"
     },
     "pro": {
       "name": "Pro",
@@ -5100,13 +5290,44 @@
       "error": "Failed to open billing portal"
     }
   },
+  "upgradeBanner": {
+    "title": "Upgrade to Server Plan",
+    "message": "Get the most out of Stirling PDF with unlimited users and advanced features",
+    "upgradeButton": "Upgrade Now",
+    "dismiss": "Dismiss banner"
+  },
   "payment": {
     "preparing": "Preparing your checkout...",
     "upgradeTitle": "Upgrade to {{planName}}",
     "success": "Payment Successful!",
     "successMessage": "Your subscription has been activated successfully. You will receive a confirmation email shortly.",
     "autoClose": "This window will close automatically...",
-    "error": "Payment Error"
+    "error": "Payment Error",
+    "upgradeSuccess": "Payment successful! Your subscription has been upgraded. The license has been updated on your server. You will receive a confirmation email shortly.",
+    "paymentSuccess": "Payment successful! Retrieving your license key...",
+    "licenseActivated": "License activated! Your license key has been saved. A confirmation email has been sent to your registered email address.",
+    "licenseDelayed": "Payment successful! Your license is being generated. You will receive an email with your license key shortly. If you don't receive it within 10 minutes, please contact support.",
+    "licensePollingError": "Payment successful but we couldn't retrieve your license key automatically. Please check your email or contact support with your payment confirmation.",
+    "licenseRetrievalError": "Payment successful but license retrieval failed. You will receive your license key via email. Please contact support if you don't receive it within 10 minutes.",
+    "syncError": "Payment successful but license sync failed. Your license will be updated shortly. Please contact support if issues persist.",
+    "licenseSaveError": "Failed to save license key. Please contact support with your license key to complete activation.",
+    "paymentCanceled": "Payment was canceled. No charges were made.",
+    "syncingLicense": "Syncing your upgraded license...",
+    "generatingLicense": "Generating your license key...",
+    "upgradeComplete": "Upgrade Complete",
+    "upgradeCompleteMessage": "Your subscription has been upgraded successfully. Your existing license key has been updated.",
+    "stripeNotConfigured": "Stripe Not Configured",
+    "stripeNotConfiguredMessage": "Stripe payment integration is not configured. Please contact your administrator.",
+    "monthly": "Monthly",
+    "yearly": "Yearly",
+    "billingPeriod": "Billing Period",
+    "enterpriseNote": "Seats can be adjusted in checkout (1-1000).",
+    "installationId": "Installation ID",
+    "licenseKey": "Your License Key",
+    "licenseInstructions": "Enter this key in Settings → Admin Plan → License Key section",
+    "canCloseWindow": "You can now close this window.",
+    "licenseKeyProcessing": "License Key Processing",
+    "licenseDelayedMessage": "Your license key is being generated. Please check your email shortly or contact support."
   },
   "firstLogin": {
     "title": "First Time Login",
@@ -5262,6 +5483,145 @@
   "backendHealth": {
     "checking": "Checking backend status...",
     "online": "Backend Online",
-    "offline": "Backend Offline"
+    "offline": "Backend Offline",
+    "starting": "Backend starting up...",
+    "wait": "Please wait for the backend to finish launching and try again."
+  },
+  "setup": {
+    "welcome": "Welcome to Stirling PDF",
+    "description": "Get started by choosing how you want to use Stirling PDF",
+    "step1": {
+      "label": "Choose Mode",
+      "description": "Offline or Server"
+    },
+    "step2": {
+      "label": "Select Server",
+      "description": "Self-hosted server"
+    },
+    "step3": {
+      "label": "Login",
+      "description": "Enter credentials"
+    },
+    "mode": {
+      "offline": {
+        "title": "Use Offline",
+        "description": "Run locally without an internet connection"
+      },
+      "server": {
+        "title": "Connect to Server",
+        "description": "Connect to a remote Stirling PDF server"
+      }
+    },
+    "server": {
+      "title": "Connect to Server",
+      "subtitle": "Enter your self-hosted server URL",
+      "type": {
+        "saas": "Stirling PDF SaaS",
+        "selfhosted": "Self-hosted server"
+      },
+      "url": {
+        "label": "Server URL",
+        "description": "Enter the full URL of your self-hosted Stirling PDF server"
+      },
+      "error": {
+        "emptyUrl": "Please enter a server URL",
+        "unreachable": "Could not connect to server",
+        "testFailed": "Connection test failed"
+      },
+      "testing": "Testing connection..."
+    },
+    "login": {
+      "title": "Sign In",
+      "subtitle": "Enter your credentials to continue",
+      "connectingTo": "Connecting to:",
+      "username": {
+        "label": "Username",
+        "placeholder": "Enter your username"
+      },
+      "password": {
+        "label": "Password",
+        "placeholder": "Enter your password"
+      },
+      "error": {
+        "emptyUsername": "Please enter your username",
+        "emptyPassword": "Please enter your password"
+      },
+      "submit": "Login"
+    }
+  },
+  "settings": {
+    "connection": {
+      "title": "Connection Mode",
+      "mode": {
+        "offline": "Offline",
+        "server": "Server"
+      },
+      "server": "Server",
+      "user": "Logged in as",
+      "switchToServer": "Connect to Server",
+      "switchToOffline": "Switch to Offline",
+      "logout": "Logout",
+      "selectServer": "Select Server",
+      "login": "Login"
+    },
+    "general": {
+      "title": "General",
+      "description": "Configure general application preferences.",
+      "user": "User",
+      "logout": "Log out",
+      "enableFeatures": {
+        "dismiss": "Dismiss",
+        "title": "For System Administrators",
+        "intro": "Enable user authentication, team management, and workspace features for your organisation.",
+        "action": "Configure",
+        "and": "and",
+        "benefit": "Enables user roles, team collaboration, admin controls, and enterprise features.",
+        "learnMore": "Learn more in documentation"
+      },
+      "defaultToolPickerMode": "Default tool picker mode",
+      "defaultToolPickerModeDescription": "Choose whether the tool picker opens in fullscreen or sidebar by default",
+      "mode": {
+        "sidebar": "Sidebar",
+        "fullscreen": "Fullscreen"
+      },
+      "autoUnzipTooltip": "Automatically extract ZIP files returned from API operations. Disable to keep ZIP files intact. This does not affect automation workflows.",
+      "autoUnzip": "Auto-unzip API responses",
+      "autoUnzipDescription": "Automatically extract files from ZIP responses",
+      "autoUnzipFileLimitTooltip": "Only unzip if the ZIP contains this many files or fewer. Set higher to extract larger ZIPs.",
+      "autoUnzipFileLimit": "Auto-unzip file limit",
+      "autoUnzipFileLimitDescription": "Maximum number of files to extract from ZIP",
+      "defaultPdfEditor": "Default PDF editor",
+      "defaultPdfEditorActive": "Stirling PDF is your default PDF editor",
+      "defaultPdfEditorInactive": "Another application is set as default",
+      "defaultPdfEditorChecking": "Checking...",
+      "defaultPdfEditorSet": "Already Default",
+      "setAsDefault": "Set as Default",
+      "updates": {
+        "title": "Software Updates",
+        "description": "Check for updates and view version information",
+        "currentVersion": "Current Version",
+        "latestVersion": "Latest Version",
+        "checkForUpdates": "Check for Updates",
+        "viewDetails": "View Details"
+      }
+    },
+    "hotkeys": {
+      "errorConflict": "Shortcut already used by {{tool}}.",
+      "searchPlaceholder": "Search tools...",
+      "none": "Not assigned",
+      "customBadge": "Custom",
+      "defaultLabel": "Default: {{shortcut}}",
+      "capturing": "Press keys… (Esc to cancel)",
+      "change": "Change shortcut",
+      "reset": "Reset",
+      "shortcut": "Shortcut",
+      "noShortcut": "No shortcut set"
+    }
+  },
+  "auth": {
+    "sessionExpired": "Session Expired",
+    "pleaseLoginAgain": "Please login again.",
+    "accessDenied": "Access Denied",
+    "insufficientPermissions": "You do not have permission to perform this action."
   }
 }
diff --git a/frontend/src-tauri/Cargo.lock b/frontend/src-tauri/Cargo.lock
index c40b35a8e..7ddc3dbfd 100644
--- a/frontend/src-tauri/Cargo.lock
+++ b/frontend/src-tauri/Cargo.lock
@@ -589,10 +589,29 @@ version = "0.18.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "4ddef33a339a91ea89fb53151bd0a4689cfce27055c291dfa69945475d22c747"
 dependencies = [
+ "percent-encoding",
  "time",
  "version_check",
 ]
 
+[[package]]
+name = "cookie_store"
+version = "0.21.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "2eac901828f88a5241ee0600950ab981148a18f2f756900ffba1b125ca6a3ef9"
+dependencies = [
+ "cookie",
+ "document-features",
+ "idna",
+ "log",
+ "publicsuffix",
+ "serde",
+ "serde_derive",
+ "serde_json",
+ "time",
+ "url",
+]
+
 [[package]]
 name = "core-foundation"
 version = "0.9.4"
@@ -767,6 +786,12 @@ dependencies = [
  "syn 2.0.108",
 ]
 
+[[package]]
+name = "data-url"
+version = "0.3.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "be1e0bca6c3637f992fc1cc7cbc52a78c1ef6db076dbf1059c4323d6a2048376"
+
 [[package]]
 name = "deranged"
 version = "0.5.5"
@@ -871,6 +896,15 @@ dependencies = [
  "syn 2.0.108",
 ]
 
+[[package]]
+name = "document-features"
+version = "0.2.12"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d4b8a88685455ed29a21542a33abd9cb6510b6b129abadabdcef0f4c55bc8f61"
+dependencies = [
+ "litrs",
+]
+
 [[package]]
 name = "dpi"
 version = "0.1.2"
@@ -1365,8 +1399,10 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "335ff9f135e4384c8150d6f27c6daed433577f86b4750418338c01a1a2528592"
 dependencies = [
  "cfg-if",
+ "js-sys",
  "libc",
  "wasi 0.11.1+wasi-snapshot-preview1",
+ "wasm-bindgen",
 ]
 
 [[package]]
@@ -1376,9 +1412,11 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "899def5c37c4fd7b2664648c28120ecec138e4d395b459e5ca34f9cce2dd77fd"
 dependencies = [
  "cfg-if",
+ "js-sys",
  "libc",
  "r-efi",
  "wasip2",
+ "wasm-bindgen",
 ]
 
 [[package]]
@@ -1548,6 +1586,25 @@ dependencies = [
  "tracing",
 ]
 
+[[package]]
+name = "h2"
+version = "0.4.12"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f3c0b69cfcb4e1b9f1bf2f53f95f766e4661169728ec61cd3fe5a0166f2d1386"
+dependencies = [
+ "atomic-waker",
+ "bytes",
+ "fnv",
+ "futures-core",
+ "futures-sink",
+ "http 1.3.1",
+ "indexmap 2.12.0",
+ "slab",
+ "tokio",
+ "tokio-util",
+ "tracing",
+]
+
 [[package]]
 name = "hashbrown"
 version = "0.12.3"
@@ -1677,7 +1734,7 @@ dependencies = [
  "futures-channel",
  "futures-core",
  "futures-util",
- "h2",
+ "h2 0.3.27",
  "http 0.2.12",
  "http-body 0.4.6",
  "httparse",
@@ -1701,6 +1758,7 @@ dependencies = [
  "bytes",
  "futures-channel",
  "futures-core",
+ "h2 0.4.12",
  "http 1.3.1",
  "http-body 1.0.1",
  "httparse",
@@ -1712,6 +1770,23 @@ dependencies = [
  "want",
 ]
 
+[[package]]
+name = "hyper-rustls"
+version = "0.27.7"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e3c93eb611681b207e1fe55d5a71ecf91572ec8a6705cdb6857f7d8d5242cf58"
+dependencies = [
+ "http 1.3.1",
+ "hyper 1.7.0",
+ "hyper-util",
+ "rustls",
+ "rustls-pki-types",
+ "tokio",
+ "tokio-rustls",
+ "tower-service",
+ "webpki-roots",
+]
+
 [[package]]
 name = "hyper-tls"
 version = "0.5.0"
@@ -1744,9 +1819,11 @@ dependencies = [
  "percent-encoding",
  "pin-project-lite",
  "socket2 0.6.1",
+ "system-configuration 0.6.1",
  "tokio",
  "tower-service",
  "tracing",
+ "windows-registry",
 ]
 
 [[package]]
@@ -2057,6 +2134,16 @@ dependencies = [
  "unicode-segmentation",
 ]
 
+[[package]]
+name = "keyring"
+version = "3.6.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "eebcc3aff044e5944a8fbaf69eb277d11986064cba30c468730e8b9909fb551c"
+dependencies = [
+ "log",
+ "zeroize",
+]
+
 [[package]]
 name = "kuchikiki"
 version = "0.8.8-speedreader"
@@ -2137,6 +2224,12 @@ version = "0.8.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "241eaef5fd12c88705a01fc1066c48c4b36e0dd4377dcdc7ec3942cea7a69956"
 
+[[package]]
+name = "litrs"
+version = "1.0.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "11d3d7f243d5c5a8b9bb5d6dd2b1602c0cb0b9db1621bafc7ed66e35ff9fe092"
+
 [[package]]
 name = "lock_api"
 version = "0.4.14"
@@ -2155,6 +2248,12 @@ dependencies = [
  "value-bag",
 ]
 
+[[package]]
+name = "lru-slab"
+version = "0.1.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "112b39cec0b298b6c1999fee3e31427f74f676e4cb9879ed1a121b43661a4154"
+
 [[package]]
 name = "mac"
 version = "0.1.1"
@@ -3092,6 +3191,12 @@ dependencies = [
  "unicode-ident",
 ]
 
+[[package]]
+name = "psl-types"
+version = "2.0.11"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "33cb294fe86a74cbcf50d4445b37da762029549ebeea341421c7c70370f86cac"
+
 [[package]]
 name = "ptr_meta"
 version = "0.1.4"
@@ -3112,6 +3217,16 @@ dependencies = [
  "syn 1.0.109",
 ]
 
+[[package]]
+name = "publicsuffix"
+version = "2.3.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "6f42ea446cab60335f76979ec15e12619a2165b5ae2c12166bef27d283a9fadf"
+dependencies = [
+ "idna",
+ "psl-types",
+]
+
 [[package]]
 name = "quick-xml"
 version = "0.38.3"
@@ -3121,6 +3236,61 @@ dependencies = [
  "memchr",
 ]
 
+[[package]]
+name = "quinn"
+version = "0.11.9"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b9e20a958963c291dc322d98411f541009df2ced7b5a4f2bd52337638cfccf20"
+dependencies = [
+ "bytes",
+ "cfg_aliases",
+ "pin-project-lite",
+ "quinn-proto",
+ "quinn-udp",
+ "rustc-hash",
+ "rustls",
+ "socket2 0.6.1",
+ "thiserror 2.0.17",
+ "tokio",
+ "tracing",
+ "web-time",
+]
+
+[[package]]
+name = "quinn-proto"
+version = "0.11.13"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f1906b49b0c3bc04b5fe5d86a77925ae6524a19b816ae38ce1e426255f1d8a31"
+dependencies = [
+ "bytes",
+ "getrandom 0.3.4",
+ "lru-slab",
+ "rand 0.9.2",
+ "ring",
+ "rustc-hash",
+ "rustls",
+ "rustls-pki-types",
+ "slab",
+ "thiserror 2.0.17",
+ "tinyvec",
+ "tracing",
+ "web-time",
+]
+
+[[package]]
+name = "quinn-udp"
+version = "0.5.14"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "addec6a0dcad8a8d96a771f815f0eaf55f9d1805756410b39f5fa81332574cbd"
+dependencies = [
+ "cfg_aliases",
+ "libc",
+ "once_cell",
+ "socket2 0.6.1",
+ "tracing",
+ "windows-sys 0.60.2",
+]
+
 [[package]]
 name = "quote"
 version = "1.0.41"
@@ -3167,6 +3337,16 @@ dependencies = [
  "rand_core 0.6.4",
 ]
 
+[[package]]
+name = "rand"
+version = "0.9.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "6db2770f06117d490610c7488547d543617b21bfa07796d7a12f6f1bd53850d1"
+dependencies = [
+ "rand_chacha 0.9.0",
+ "rand_core 0.9.3",
+]
+
 [[package]]
 name = "rand_chacha"
 version = "0.2.2"
@@ -3187,6 +3367,16 @@ dependencies = [
  "rand_core 0.6.4",
 ]
 
+[[package]]
+name = "rand_chacha"
+version = "0.9.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d3022b5f1df60f26e1ffddd6c66e8aa15de382ae63b3a0c1bfc0e4d3e3f325cb"
+dependencies = [
+ "ppv-lite86",
+ "rand_core 0.9.3",
+]
+
 [[package]]
 name = "rand_core"
 version = "0.5.1"
@@ -3205,6 +3395,15 @@ dependencies = [
  "getrandom 0.2.16",
 ]
 
+[[package]]
+name = "rand_core"
+version = "0.9.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "99d9a13982dcf210057a8a78572b2217b667c3beacbf3a0d8b454f6f82837d38"
+dependencies = [
+ "getrandom 0.3.4",
+]
+
 [[package]]
 name = "rand_hc"
 version = "0.2.0"
@@ -3318,7 +3517,7 @@ dependencies = [
  "encoding_rs",
  "futures-core",
  "futures-util",
- "h2",
+ "h2 0.3.27",
  "http 0.2.12",
  "http-body 0.4.6",
  "hyper 0.14.32",
@@ -3336,7 +3535,7 @@ dependencies = [
  "serde_json",
  "serde_urlencoded",
  "sync_wrapper 0.1.2",
- "system-configuration",
+ "system-configuration 0.5.1",
  "tokio",
  "tokio-native-tls",
  "tower-service",
@@ -3355,22 +3554,32 @@ checksum = "9d0946410b9f7b082a427e4ef5c8ff541a88b357bc6c637c40db3a68ac70a36f"
 dependencies = [
  "base64 0.22.1",
  "bytes",
+ "cookie",
+ "cookie_store",
+ "encoding_rs",
  "futures-core",
  "futures-util",
+ "h2 0.4.12",
  "http 1.3.1",
  "http-body 1.0.1",
  "http-body-util",
  "hyper 1.7.0",
+ "hyper-rustls",
  "hyper-util",
  "js-sys",
  "log",
+ "mime",
  "percent-encoding",
  "pin-project-lite",
+ "quinn",
+ "rustls",
+ "rustls-pki-types",
  "serde",
  "serde_json",
  "serde_urlencoded",
  "sync_wrapper 1.0.2",
  "tokio",
+ "tokio-rustls",
  "tokio-util",
  "tower",
  "tower-http",
@@ -3380,6 +3589,21 @@ dependencies = [
  "wasm-bindgen-futures",
  "wasm-streams",
  "web-sys",
+ "webpki-roots",
+]
+
+[[package]]
+name = "ring"
+version = "0.17.14"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "a4689e6c2294d81e88dc6261c768b63bc4fcdb852be6d1352498b114f61383b7"
+dependencies = [
+ "cc",
+ "cfg-if",
+ "getrandom 0.2.16",
+ "libc",
+ "untrusted",
+ "windows-sys 0.52.0",
 ]
 
 [[package]]
@@ -3427,6 +3651,12 @@ dependencies = [
  "serde_json",
 ]
 
+[[package]]
+name = "rustc-hash"
+version = "2.1.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "357703d41365b4b27c590e3ed91eabb1b663f07c4c084095e60cbed4362dff0d"
+
 [[package]]
 name = "rustc_version"
 version = "0.4.1"
@@ -3449,6 +3679,20 @@ dependencies = [
  "windows-sys 0.61.2",
 ]
 
+[[package]]
+name = "rustls"
+version = "0.23.35"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "533f54bc6a7d4f647e46ad909549eda97bf5afc1585190ef692b4286b198bd8f"
+dependencies = [
+ "once_cell",
+ "ring",
+ "rustls-pki-types",
+ "rustls-webpki",
+ "subtle",
+ "zeroize",
+]
+
 [[package]]
 name = "rustls-pemfile"
 version = "1.0.4"
@@ -3458,6 +3702,27 @@ dependencies = [
  "base64 0.21.7",
 ]
 
+[[package]]
+name = "rustls-pki-types"
+version = "1.13.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "94182ad936a0c91c324cd46c6511b9510ed16af436d7b5bab34beab0afd55f7a"
+dependencies = [
+ "web-time",
+ "zeroize",
+]
+
+[[package]]
+name = "rustls-webpki"
+version = "0.103.8"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "2ffdfa2f5286e2247234e03f680868ac2815974dc39e00ea15adc445d0aafe52"
+dependencies = [
+ "ring",
+ "rustls-pki-types",
+ "untrusted",
+]
+
 [[package]]
 name = "rustversion"
 version = "1.0.22"
@@ -3952,6 +4217,7 @@ version = "0.1.0"
 dependencies = [
  "core-foundation 0.10.1",
  "core-services",
+ "keyring",
  "log",
  "reqwest 0.11.27",
  "serde",
@@ -3959,9 +4225,11 @@ dependencies = [
  "tauri",
  "tauri-build",
  "tauri-plugin-fs",
+ "tauri-plugin-http",
  "tauri-plugin-log",
  "tauri-plugin-shell",
  "tauri-plugin-single-instance",
+ "tauri-plugin-store",
  "tokio",
 ]
 
@@ -3996,6 +4264,12 @@ version = "0.11.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "7da8b5736845d9f2fcb837ea5d9e2628564b3b043a70948a3f0b778838c5fb4f"
 
+[[package]]
+name = "subtle"
+version = "2.6.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "13c2bddecc57b384dee18652358fb23172facb8a2c51ccc10d74c157bdea3292"
+
 [[package]]
 name = "swift-rs"
 version = "1.0.7"
@@ -4063,7 +4337,18 @@ checksum = "ba3a3adc5c275d719af8cb4272ea1c4a6d668a777f37e115f6d11ddbc1c8e0e7"
 dependencies = [
  "bitflags 1.3.2",
  "core-foundation 0.9.4",
- "system-configuration-sys",
+ "system-configuration-sys 0.5.0",
+]
+
+[[package]]
+name = "system-configuration"
+version = "0.6.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "3c879d448e9d986b661742763247d3693ed13609438cf3d006f51f5368a5ba6b"
+dependencies = [
+ "bitflags 2.10.0",
+ "core-foundation 0.9.4",
+ "system-configuration-sys 0.6.0",
 ]
 
 [[package]]
@@ -4076,6 +4361,16 @@ dependencies = [
  "libc",
 ]
 
+[[package]]
+name = "system-configuration-sys"
+version = "0.6.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "8e1d1b10ced5ca923a1fcb8d03e96b8d3268065d724548c0211415ff6ac6bac4"
+dependencies = [
+ "core-foundation-sys",
+ "libc",
+]
+
 [[package]]
 name = "system-deps"
 version = "6.2.2"
@@ -4305,6 +4600,30 @@ dependencies = [
  "url",
 ]
 
+[[package]]
+name = "tauri-plugin-http"
+version = "2.5.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "c00685aceab12643cf024f712ab0448ba8fcadf86f2391d49d2e5aa732aacc70"
+dependencies = [
+ "bytes",
+ "cookie_store",
+ "data-url",
+ "http 1.3.1",
+ "regex",
+ "reqwest 0.12.24",
+ "schemars 0.8.22",
+ "serde",
+ "serde_json",
+ "tauri",
+ "tauri-plugin",
+ "tauri-plugin-fs",
+ "thiserror 2.0.17",
+ "tokio",
+ "url",
+ "urlpattern",
+]
+
 [[package]]
 name = "tauri-plugin-log"
 version = "2.7.1"
@@ -4363,6 +4682,22 @@ dependencies = [
  "zbus",
 ]
 
+[[package]]
+name = "tauri-plugin-store"
+version = "2.4.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "59a77036340a97eb5bbe1b3209c31e5f27f75e6f92a52fd9dd4b211ef08bf310"
+dependencies = [
+ "dunce",
+ "serde",
+ "serde_json",
+ "tauri",
+ "tauri-plugin",
+ "thiserror 2.0.17",
+ "tokio",
+ "tracing",
+]
+
 [[package]]
 name = "tauri-runtime"
 version = "2.9.1"
@@ -4596,9 +4931,21 @@ dependencies = [
  "mio",
  "pin-project-lite",
  "socket2 0.6.1",
+ "tokio-macros",
  "windows-sys 0.61.2",
 ]
 
+[[package]]
+name = "tokio-macros"
+version = "2.6.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "af407857209536a95c8e56f8231ef2c2e2aff839b22e07a1ffcbc617e9db9fa5"
+dependencies = [
+ "proc-macro2",
+ "quote",
+ "syn 2.0.108",
+]
+
 [[package]]
 name = "tokio-native-tls"
 version = "0.3.1"
@@ -4609,6 +4956,16 @@ dependencies = [
  "tokio",
 ]
 
+[[package]]
+name = "tokio-rustls"
+version = "0.26.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "1729aa945f29d91ba541258c8df89027d5792d85a8841fb65e8bf0f4ede4ef61"
+dependencies = [
+ "rustls",
+ "tokio",
+]
+
 [[package]]
 name = "tokio-util"
 version = "0.7.16"
@@ -4898,6 +5255,12 @@ version = "1.12.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "f6ccf251212114b54433ec949fd6a7841275f9ada20dddd2f29e9ceea4501493"
 
+[[package]]
+name = "untrusted"
+version = "0.9.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "8ecb6da28b8a351d773b68d5825ac39017e680750f980f3a1a85cd8dd28a47c1"
+
 [[package]]
 name = "url"
 version = "2.5.7"
@@ -5131,6 +5494,16 @@ dependencies = [
  "wasm-bindgen",
 ]
 
+[[package]]
+name = "web-time"
+version = "1.1.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "5a6580f308b1fad9207618087a65c04e7a10bc77e02c8e84e9b00dd4b12fa0bb"
+dependencies = [
+ "js-sys",
+ "wasm-bindgen",
+]
+
 [[package]]
 name = "webkit2gtk"
 version = "2.0.1"
@@ -5175,6 +5548,15 @@ dependencies = [
  "system-deps",
 ]
 
+[[package]]
+name = "webpki-roots"
+version = "1.0.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b2878ef029c47c6e8cf779119f20fcf52bde7ad42a731b2a304bc221df17571e"
+dependencies = [
+ "rustls-pki-types",
+]
+
 [[package]]
 name = "webview2-com"
 version = "0.38.0"
@@ -5360,6 +5742,17 @@ dependencies = [
  "windows-link 0.1.3",
 ]
 
+[[package]]
+name = "windows-registry"
+version = "0.5.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "5b8a9ed28765efc97bbc954883f4e6796c33a06546ebafacbabee9696967499e"
+dependencies = [
+ "windows-link 0.1.3",
+ "windows-result 0.3.4",
+ "windows-strings 0.4.2",
+]
+
 [[package]]
 name = "windows-result"
 version = "0.3.4"
@@ -5962,6 +6355,12 @@ dependencies = [
  "synstructure",
 ]
 
+[[package]]
+name = "zeroize"
+version = "1.8.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b97154e67e32c85465826e8bcc1c59429aaaf107c1e4a9e53c8d8ccd5eff88d0"
+
 [[package]]
 name = "zerotrie"
 version = "0.2.2"
diff --git a/frontend/src-tauri/Cargo.toml b/frontend/src-tauri/Cargo.toml
index b75106195..968edc53d 100644
--- a/frontend/src-tauri/Cargo.toml
+++ b/frontend/src-tauri/Cargo.toml
@@ -28,7 +28,10 @@ tauri = { version = "2.9.0", features = [ "devtools"] }
 tauri-plugin-log = "2.0.0-rc"
 tauri-plugin-shell = "2.1.0"
 tauri-plugin-fs = "2.4.4"
+tauri-plugin-http = "2.4.4"
 tauri-plugin-single-instance = "2.0.1"
+tauri-plugin-store = "2.1.0"
+keyring = "3.6.1"
 tokio = { version = "1.0", features = ["time"] }
 reqwest = { version = "0.11", features = ["json"] }
 
diff --git a/frontend/src-tauri/capabilities/default.json b/frontend/src-tauri/capabilities/default.json
index 385973667..b6f98d92e 100644
--- a/frontend/src-tauri/capabilities/default.json
+++ b/frontend/src-tauri/capabilities/default.json
@@ -7,9 +7,18 @@
   ],
   "permissions": [
     "core:default",
-    { 
-    "identifier": "fs:allow-read-file",
-    "allow": [{ "path": "**" }]
-   }
+    "http:default",
+    {
+      "identifier": "http:allow-fetch",
+      "allow": [
+        { "url": "http://localhost:*" },
+        { "url": "http://127.0.0.1:*" },
+        { "url": "https://*" }
+      ]
+    },
+    {
+      "identifier": "fs:allow-read-file",
+      "allow": [{ "path": "**" }]
+    }
   ]
 }
diff --git a/frontend/src-tauri/src/commands/auth.rs b/frontend/src-tauri/src/commands/auth.rs
new file mode 100644
index 000000000..9ce4c3cda
--- /dev/null
+++ b/frontend/src-tauri/src/commands/auth.rs
@@ -0,0 +1,215 @@
+use keyring::Entry;
+use serde::{Deserialize, Serialize};
+use tauri::AppHandle;
+use tauri_plugin_store::StoreExt;
+
+const STORE_FILE: &str = "connection.json";
+const USER_INFO_KEY: &str = "user_info";
+const KEYRING_SERVICE: &str = "stirling-pdf";
+const KEYRING_TOKEN_KEY: &str = "auth-token";
+
+#[derive(Debug, Serialize, Deserialize, Clone)]
+pub struct UserInfo {
+    pub username: String,
+    pub email: Option<String>,
+}
+
+fn get_keyring_entry() -> Result<Entry, String> {
+    Entry::new(KEYRING_SERVICE, KEYRING_TOKEN_KEY)
+        .map_err(|e| format!("Failed to access keyring: {}", e))
+}
+
+#[tauri::command]
+pub async fn save_auth_token(_app_handle: AppHandle, token: String) -> Result<(), String> {
+    log::info!("Saving auth token to keyring");
+
+    let entry = get_keyring_entry()?;
+
+    entry
+        .set_password(&token)
+        .map_err(|e| format!("Failed to save token to keyring: {}", e))?;
+
+    log::info!("Auth token saved successfully");
+    Ok(())
+}
+
+#[tauri::command]
+pub async fn get_auth_token(_app_handle: AppHandle) -> Result<Option<String>, String> {
+    log::debug!("Retrieving auth token from keyring");
+
+    let entry = get_keyring_entry()?;
+
+    match entry.get_password() {
+        Ok(token) => Ok(Some(token)),
+        Err(keyring::Error::NoEntry) => Ok(None),
+        Err(e) => Err(format!("Failed to retrieve token: {}", e)),
+    }
+}
+
+#[tauri::command]
+pub async fn clear_auth_token(_app_handle: AppHandle) -> Result<(), String> {
+    log::info!("Clearing auth token from keyring");
+
+    let entry = get_keyring_entry()?;
+
+    // Delete the token - ignore error if it doesn't exist
+    match entry.delete_credential() {
+        Ok(_) => {
+            log::info!("Auth token cleared successfully");
+            Ok(())
+        }
+        Err(keyring::Error::NoEntry) => {
+            log::info!("Auth token was already cleared");
+            Ok(())
+        }
+        Err(e) => Err(format!("Failed to clear token: {}", e)),
+    }
+}
+
+#[tauri::command]
+pub async fn save_user_info(
+    app_handle: AppHandle,
+    username: String,
+    email: Option<String>,
+) -> Result<(), String> {
+    log::info!("Saving user info for: {}", username);
+
+    let user_info = UserInfo { username, email };
+
+    let store = app_handle
+        .store(STORE_FILE)
+        .map_err(|e| format!("Failed to access store: {}", e))?;
+
+    store.set(
+        USER_INFO_KEY,
+        serde_json::to_value(&user_info)
+            .map_err(|e| format!("Failed to serialize user info: {}", e))?,
+    );
+
+    store
+        .save()
+        .map_err(|e| format!("Failed to save store: {}", e))?;
+
+    log::info!("User info saved successfully");
+    Ok(())
+}
+
+#[tauri::command]
+pub async fn get_user_info(app_handle: AppHandle) -> Result<Option<UserInfo>, String> {
+    log::debug!("Retrieving user info");
+
+    let store = app_handle
+        .store(STORE_FILE)
+        .map_err(|e| format!("Failed to access store: {}", e))?;
+
+    let user_info: Option<UserInfo> = store
+        .get(USER_INFO_KEY)
+        .and_then(|v| serde_json::from_value(v.clone()).ok());
+
+    Ok(user_info)
+}
+
+#[tauri::command]
+pub async fn clear_user_info(app_handle: AppHandle) -> Result<(), String> {
+    log::info!("Clearing user info");
+
+    let store = app_handle
+        .store(STORE_FILE)
+        .map_err(|e| format!("Failed to access store: {}", e))?;
+
+    store.delete(USER_INFO_KEY);
+
+    store
+        .save()
+        .map_err(|e| format!("Failed to save store: {}", e))?;
+
+    log::info!("User info cleared successfully");
+    Ok(())
+}
+
+// Response types for Spring Boot login
+#[derive(Debug, Deserialize)]
+struct SpringBootSession {
+    access_token: String,
+}
+
+#[derive(Debug, Deserialize)]
+struct SpringBootUser {
+    username: String,
+    email: Option<String>,
+}
+
+#[derive(Debug, Deserialize)]
+struct SpringBootLoginResponse {
+    session: SpringBootSession,
+    user: SpringBootUser,
+}
+
+#[derive(Debug, Serialize)]
+pub struct LoginResponse {
+    pub token: String,
+    pub username: String,
+    pub email: Option<String>,
+}
+
+/// Login command - makes HTTP request from Rust to bypass CORS
+/// Supports Spring Boot authentication (self-hosted)
+#[tauri::command]
+pub async fn login(
+    server_url: String,
+    username: String,
+    password: String,
+) -> Result<LoginResponse, String> {
+    log::info!("Login attempt for user: {} to server: {}", username, server_url);
+
+    // Build login URL
+    let login_url = format!("{}/api/v1/auth/login", server_url.trim_end_matches('/'));
+    log::debug!("Login URL: {}", login_url);
+
+    // Create HTTP client
+    let client = reqwest::Client::new();
+
+    // Make login request
+    let response = client
+        .post(&login_url)
+        .json(&serde_json::json!({
+            "username": username,
+            "password": password,
+        }))
+        .send()
+        .await
+        .map_err(|e| format!("Network error: {}", e))?;
+
+    let status = response.status();
+    log::debug!("Login response status: {}", status);
+
+    if !status.is_success() {
+        let error_text = response
+            .text()
+            .await
+            .unwrap_or_else(|_| "Unknown error".to_string());
+        log::error!("Login failed with status {}: {}", status, error_text);
+
+        return Err(if status.as_u16() == 401 {
+            "Invalid username or password".to_string()
+        } else if status.as_u16() == 403 {
+            "Access denied".to_string()
+        } else {
+            format!("Login failed: {}", status)
+        });
+    }
+
+    // Parse Spring Boot response format
+    let login_response: SpringBootLoginResponse = response
+        .json()
+        .await
+        .map_err(|e| format!("Failed to parse response: {}", e))?;
+
+    log::info!("Login successful for user: {}", login_response.user.username);
+
+    Ok(LoginResponse {
+        token: login_response.session.access_token,
+        username: login_response.user.username,
+        email: login_response.user.email,
+    })
+}
diff --git a/frontend/src-tauri/src/commands/backend.rs b/frontend/src-tauri/src/commands/backend.rs
index c7bce50f7..27a4a7dfd 100644
--- a/frontend/src-tauri/src/commands/backend.rs
+++ b/frontend/src-tauri/src/commands/backend.rs
@@ -3,10 +3,12 @@ use tauri::Manager;
 use std::sync::Mutex;
 use std::path::PathBuf;
 use crate::utils::add_log;
+use crate::state::connection_state::{AppConnectionState, ConnectionMode};
 
-// Store backend process handle globally
+// Store backend process handle and port globally
 static BACKEND_PROCESS: Mutex<Option<tauri_plugin_shell::process::CommandChild>> = Mutex::new(None);
 static BACKEND_STARTING: Mutex<bool> = Mutex::new(false);
+static BACKEND_PORT: Mutex<Option<u16>> = Mutex::new(None);
 
 // Helper function to reset starting flag
 fn reset_starting_flag() {
@@ -14,6 +16,20 @@ fn reset_starting_flag() {
     *starting_guard = false;
 }
 
+// Extract port number from "Stirling-PDF running on port: PORT" log line
+fn extract_port_from_running_log(log_line: &str) -> Option<u16> {
+    // Look for pattern: "running on port: PORT"
+    if let Some(start) = log_line.find("running on port: ") {
+        let after_prefix = &log_line[start + 17..]; // Skip "running on port: "
+        // Take digits until whitespace or end of line
+        let port_str: String = after_prefix.chars()
+            .take_while(|c| c.is_ascii_digit())
+            .collect();
+        return port_str.parse::<u16>().ok();
+    }
+    None
+}
+
 // Check if backend is already running or starting
 fn check_backend_status() -> Result<(), String> {
     // Check if backend is already running
@@ -24,7 +40,7 @@ fn check_backend_status() -> Result<(), String> {
             return Err("Backend already running".to_string());
         }
     }
-    
+
     // Check and set starting flag to prevent multiple simultaneous starts
     {
         let mut starting_guard = BACKEND_STARTING.lock().unwrap();
@@ -34,7 +50,7 @@ fn check_backend_status() -> Result<(), String> {
         }
         *starting_guard = true;
     }
-    
+
     Ok(())
 }
 
@@ -46,13 +62,13 @@ fn find_bundled_jre(resource_dir: &PathBuf) -> Result<PathBuf, String> {
     } else {
         jre_dir.join("bin").join("java")
     };
-    
+
     if !java_executable.exists() {
         let error_msg = format!("❌ Bundled JRE not found at: {:?}", java_executable);
         add_log(error_msg.clone());
         return Err(error_msg);
     }
-    
+
     add_log(format!("✅ Found bundled JRE: {:?}", java_executable));
     Ok(java_executable)
 }
@@ -77,20 +93,20 @@ fn find_stirling_jar(resource_dir: &PathBuf) -> Result<PathBuf, String> {
                     .unwrap_or(false)
         })
         .collect();
-    
+
     if jar_files.is_empty() {
         let error_msg = "No Stirling-PDF JAR found in libs directory.".to_string();
         add_log(error_msg.clone());
         return Err(error_msg);
     }
-    
+
     // Sort by filename to get the latest version (case-insensitive)
     jar_files.sort_by(|a, b| {
         let name_a = a.file_name().to_string_lossy().to_ascii_lowercase();
         let name_b = b.file_name().to_string_lossy().to_ascii_lowercase();
         name_b.cmp(&name_a) // Reverse order to get latest first
     });
-    
+
     let jar_path = jar_files[0].path();
     add_log(format!("📋 Selected JAR: {:?}", jar_path.file_name().unwrap()));
     Ok(jar_path)
@@ -123,23 +139,23 @@ fn run_stirling_pdf_jar(app: &tauri::AppHandle, java_path: &PathBuf, jar_path: &
         let home = std::env::var("HOME").unwrap_or_else(|_| "/tmp".to_string());
         PathBuf::from(home).join(".config").join("Stirling-PDF")
     };
-    
+
     // Create subdirectories for different purposes
     let config_dir = app_data_dir.join("configs");
     let log_dir = app_data_dir.join("logs");
     let work_dir = app_data_dir.join("workspace");
-    
+
     // Create all necessary directories
     std::fs::create_dir_all(&app_data_dir).ok();
     std::fs::create_dir_all(&log_dir).ok();
     std::fs::create_dir_all(&work_dir).ok();
     std::fs::create_dir_all(&config_dir).ok();
-    
+
     add_log(format!("📁 App data directory: {}", app_data_dir.display()));
     add_log(format!("📁 Log directory: {}", log_dir.display()));
     add_log(format!("📁 Working directory: {}", work_dir.display()));
     add_log(format!("📁 Config directory: {}", config_dir.display()));
-    
+
     // Define all Java options with Tauri-specific paths
     let log_path_option = format!("-Dlogging.file.path={}", log_dir.display());
 
@@ -150,10 +166,13 @@ fn run_stirling_pdf_jar(app: &tauri::AppHandle, java_path: &PathBuf, jar_path: &
         "-DSTIRLING_PDF_TAURI_MODE=true",
         &log_path_option,
         "-Dlogging.file.name=stirling-pdf.log",
+        "-Dserver.port=0",  // Let OS assign an available port
+        "-Dsecurity.enableLogin=false",  // Disable login for desktop mode
+        "-Dsecurity.csrfDisabled=true",  // Disable CSRF for desktop mode
         "-jar",
-        jar_path.to_str().unwrap()
+        jar_path.to_str().unwrap(),
     ];
-    
+
     // Log the equivalent command for external testing
     let java_command = format!(
         "TAURI_PARENT_PID={} \"{}\" {}",
@@ -163,14 +182,14 @@ fn run_stirling_pdf_jar(app: &tauri::AppHandle, java_path: &PathBuf, jar_path: &
     );
     add_log(format!("🔧 Equivalent command: {}", java_command));
     add_log(format!("📁 Backend logs will be in: {}", log_dir.display()));
-    
+
     // Additional macOS-specific checks
     if cfg!(target_os = "macos") {
         // Check if java executable has execute permissions
         if let Ok(metadata) = std::fs::metadata(java_path) {
             let permissions = metadata.permissions();
             add_log(format!("🔍 Java executable permissions: {:?}", permissions));
-            
+
             #[cfg(unix)]
             {
                 use std::os::unix::fs::PermissionsExt;
@@ -181,7 +200,7 @@ fn run_stirling_pdf_jar(app: &tauri::AppHandle, java_path: &PathBuf, jar_path: &
                 }
             }
         }
-        
+
         // Check if we can read the JAR file
         if let Ok(metadata) = std::fs::metadata(jar_path) {
             add_log(format!("📦 JAR file size: {} bytes", metadata.len()));
@@ -189,7 +208,7 @@ fn run_stirling_pdf_jar(app: &tauri::AppHandle, java_path: &PathBuf, jar_path: &
             add_log("⚠️ Cannot read JAR file metadata".to_string());
         }
     }
-    
+
     let sidecar_command = app
         .shell()
         .command(java_path.to_str().unwrap())
@@ -199,9 +218,9 @@ fn run_stirling_pdf_jar(app: &tauri::AppHandle, java_path: &PathBuf, jar_path: &
         .env("STIRLING_PDF_CONFIG_DIR", config_dir.to_str().unwrap())
         .env("STIRLING_PDF_LOG_DIR", log_dir.to_str().unwrap())
         .env("STIRLING_PDF_WORK_DIR", work_dir.to_str().unwrap());
-    
+
     add_log("⚙️ Starting backend with bundled JRE...".to_string());
-    
+
     let (rx, child) = sidecar_command
         .spawn()
         .map_err(|e| {
@@ -209,18 +228,18 @@ fn run_stirling_pdf_jar(app: &tauri::AppHandle, java_path: &PathBuf, jar_path: &
             add_log(error_msg.clone());
             error_msg
         })?;
-    
+
     // Store the process handle
     {
         let mut process_guard = BACKEND_PROCESS.lock().unwrap();
         *process_guard = Some(child);
     }
-    
+
     add_log("✅ Backend started with bundled JRE, monitoring output...".to_string());
-    
+
     // Start monitoring output
     monitor_backend_output(rx);
-    
+
     Ok(())
 }
 
@@ -229,7 +248,7 @@ fn monitor_backend_output(mut rx: tauri::async_runtime::Receiver<tauri_plugin_sh
     tokio::spawn(async move {
         let mut _startup_detected = false;
         let mut error_count = 0;
-        
+
         while let Some(event) = rx.recv().await {
             match event {
                 tauri_plugin_shell::process::CommandEvent::Stdout(output) => {
@@ -237,17 +256,22 @@ fn monitor_backend_output(mut rx: tauri::async_runtime::Receiver<tauri_plugin_sh
                     // Strip exactly one trailing newline to avoid double newlines
                     let output_str = output_str.strip_suffix('\n').unwrap_or(&output_str);
                     add_log(format!("📤 Backend: {}", output_str));
-                    
-                    // Look for startup indicators
-                    if output_str.contains("Started SPDFApplication") || 
-                       output_str.contains("Navigate to "){
+
+                    // Look for actual runtime port from web server initialization
+                    // Format: "Stirling-PDF running on port: PORT"
+                    if output_str.contains("running on port:") {
                         _startup_detected = true;
-                        add_log(format!("🎉 Backend startup detected: {}", output_str));
+                        if let Some(port) = extract_port_from_running_log(&output_str) {
+                            let mut port_guard = BACKEND_PORT.lock().unwrap();
+                            *port_guard = Some(port);
+                            add_log(format!("🎉 Backend started on port: {}", port));
+                            add_log(format!("🔌 Navigate to: http://localhost:{}/", port));
+                        }
                     }
-                    
-                    // Look for port binding
-                    if output_str.contains("8080") {
-                        add_log(format!("🔌 Port 8080 related output: {}", output_str));
+
+                    if output_str.contains("Started SPDFApplication") {
+                        _startup_detected = true;
+                        add_log(format!("🎉 Backend startup completed: {}", output_str));
                     }
                 }
                 tauri_plugin_shell::process::CommandEvent::Stderr(output) => {
@@ -255,13 +279,13 @@ fn monitor_backend_output(mut rx: tauri::async_runtime::Receiver<tauri_plugin_sh
                     // Strip exactly one trailing newline to avoid double newlines
                     let output_str = output_str.strip_suffix('\n').unwrap_or(&output_str);
                     add_log(format!("📥 Backend Error: {}", output_str));
-                    
+
                     // Look for error indicators
                     if output_str.contains("ERROR") || output_str.contains("Exception") || output_str.contains("FATAL") {
                         error_count += 1;
                         add_log(format!("⚠️ Backend error #{}: {}", error_count, output_str));
                     }
-                    
+
                     // Look for specific common issues
                     if output_str.contains("Address already in use") {
                         add_log("🚨 CRITICAL: Port 8080 is already in use by another process!".to_string());
@@ -299,7 +323,7 @@ fn monitor_backend_output(mut rx: tauri::async_runtime::Receiver<tauri_plugin_sh
                 }
             }
         }
-        
+
         if error_count > 0 {
             println!("⚠️ Backend process ended with {} errors detected", error_count);
         }
@@ -308,14 +332,36 @@ fn monitor_backend_output(mut rx: tauri::async_runtime::Receiver<tauri_plugin_sh
 
 // Command to start the backend with bundled JRE
 #[tauri::command]
-pub async fn start_backend(app: tauri::AppHandle) -> Result<String, String> {
+pub async fn start_backend(
+    app: tauri::AppHandle,
+    connection_state: tauri::State<'_, AppConnectionState>,
+) -> Result<String, String> {
     add_log("🚀 start_backend() called - Attempting to start backend with bundled JRE...".to_string());
-    
+
+    // Check connection mode
+    let mode = {
+        let state = connection_state.0.lock().map_err(|e| {
+            let error_msg = format!("❌ Failed to access connection state: {}", e);
+            add_log(error_msg.clone());
+            error_msg
+        })?;
+        state.mode.clone()
+    };
+
+    match mode {
+        ConnectionMode::Offline => {
+            add_log("🔌 Running in Offline mode - starting local backend".to_string());
+        }
+        ConnectionMode::Server => {
+            add_log("🌐 Running in Server mode - starting local backend (for hybrid execution support)".to_string());
+        }
+    }
+
     // Check if backend is already running or starting
     if let Err(msg) = check_backend_status() {
         return Ok(msg);
     }
-    
+
     // Use Tauri's resource API to find the bundled JRE and JAR
     let resource_dir = app.path().resource_dir().map_err(|e| {
         let error_msg = format!("❌ Failed to get resource directory: {}", e);
@@ -323,53 +369,60 @@ pub async fn start_backend(app: tauri::AppHandle) -> Result<String, String> {
         reset_starting_flag();
         error_msg
     })?;
-    
+
     add_log(format!("🔍 Resource directory: {:?}", resource_dir));
-    
+
     // Find the bundled JRE
     let java_executable = find_bundled_jre(&resource_dir).map_err(|e| {
         reset_starting_flag();
         e
     })?;
-    
+
     // Find the Stirling-PDF JAR
     let jar_path = find_stirling_jar(&resource_dir).map_err(|e| {
         reset_starting_flag();
         e
     })?;
-    
+
     // Normalize the paths to remove Windows UNC prefix
     let normalized_java_path = normalize_path(&java_executable);
     let normalized_jar_path = normalize_path(&jar_path);
-    
+
     add_log(format!("📦 Found JAR file: {:?}", jar_path));
     add_log(format!("📦 Normalized JAR path: {:?}", normalized_jar_path));
     add_log(format!("📦 Normalized Java path: {:?}", normalized_java_path));
-    
+
     // Create and start the Java command
     run_stirling_pdf_jar(&app, &normalized_java_path, &normalized_jar_path).map_err(|e| {
         reset_starting_flag();
         e
     })?;
-    
+
     // Wait for the backend to start
     println!("⏳ Waiting for backend startup...");
     tokio::time::sleep(std::time::Duration::from_millis(10000)).await;
-    
+
     // Reset the starting flag since startup is complete
     reset_starting_flag();
     add_log("✅ Backend startup sequence completed, starting flag cleared".to_string());
-    
+
     Ok("Backend startup initiated successfully with bundled JRE".to_string())
 }
 
+// Get the dynamically assigned backend port
+#[tauri::command]
+pub fn get_backend_port() -> Option<u16> {
+    let port_guard = BACKEND_PORT.lock().unwrap();
+    *port_guard
+}
+
 // Cleanup function to stop backend on app exit
 pub fn cleanup_backend() {
     let mut process_guard = BACKEND_PROCESS.lock().unwrap();
     if let Some(child) = process_guard.take() {
         let pid = child.pid();
         add_log(format!("🧹 App shutting down, cleaning up backend process (PID: {})", pid));
-        
+
         match child.kill() {
             Ok(_) => {
                 add_log(format!("✅ Backend process (PID: {}) terminated during cleanup", pid));
@@ -380,4 +433,4 @@ pub fn cleanup_backend() {
             }
         }
     }
-}
\ No newline at end of file
+}
diff --git a/frontend/src-tauri/src/commands/connection.rs b/frontend/src-tauri/src/commands/connection.rs
new file mode 100644
index 000000000..097d411b5
--- /dev/null
+++ b/frontend/src-tauri/src/commands/connection.rs
@@ -0,0 +1,111 @@
+use crate::state::connection_state::{
+    AppConnectionState,
+    ConnectionMode,
+    ServerConfig,
+};
+use serde::{Deserialize, Serialize};
+use tauri::{AppHandle, State};
+use tauri_plugin_store::StoreExt;
+
+const STORE_FILE: &str = "connection.json";
+const FIRST_LAUNCH_KEY: &str = "setup_completed";
+const CONNECTION_MODE_KEY: &str = "connection_mode";
+const SERVER_CONFIG_KEY: &str = "server_config";
+
+#[derive(Debug, Serialize, Deserialize)]
+pub struct ConnectionConfig {
+    pub mode: ConnectionMode,
+    pub server_config: Option<ServerConfig>,
+}
+
+#[tauri::command]
+pub async fn get_connection_config(
+    app_handle: AppHandle,
+    state: State<'_, AppConnectionState>,
+) -> Result<ConnectionConfig, String> {
+    // Try to load from store
+    let store = app_handle
+        .store(STORE_FILE)
+        .map_err(|e| format!("Failed to access store: {}", e))?;
+
+    let mode = store
+        .get(CONNECTION_MODE_KEY)
+        .and_then(|v| serde_json::from_value(v.clone()).ok())
+        .unwrap_or(ConnectionMode::Offline);
+
+    let server_config: Option<ServerConfig> = store
+        .get(SERVER_CONFIG_KEY)
+        .and_then(|v| serde_json::from_value(v.clone()).ok());
+
+    // Update in-memory state
+    if let Ok(mut conn_state) = state.0.lock() {
+        conn_state.mode = mode.clone();
+        conn_state.server_config = server_config.clone();
+    }
+
+    Ok(ConnectionConfig {
+        mode,
+        server_config,
+    })
+}
+
+#[tauri::command]
+pub async fn set_connection_mode(
+    app_handle: AppHandle,
+    state: State<'_, AppConnectionState>,
+    mode: ConnectionMode,
+    server_config: Option<ServerConfig>,
+) -> Result<(), String> {
+    log::info!("Setting connection mode: {:?}", mode);
+
+    // Update in-memory state
+    if let Ok(mut conn_state) = state.0.lock() {
+        conn_state.mode = mode.clone();
+        conn_state.server_config = server_config.clone();
+    }
+
+    // Save to store
+    let store = app_handle
+        .store(STORE_FILE)
+        .map_err(|e| format!("Failed to access store: {}", e))?;
+
+    store.set(
+        CONNECTION_MODE_KEY,
+        serde_json::to_value(&mode).map_err(|e| format!("Failed to serialize mode: {}", e))?,
+    );
+
+    if let Some(config) = &server_config {
+        store.set(
+            SERVER_CONFIG_KEY,
+            serde_json::to_value(config)
+                .map_err(|e| format!("Failed to serialize config: {}", e))?,
+        );
+    } else {
+        store.delete(SERVER_CONFIG_KEY);
+    }
+
+    // Mark setup as completed
+    store.set(FIRST_LAUNCH_KEY, serde_json::json!(true));
+
+    store
+        .save()
+        .map_err(|e| format!("Failed to save store: {}", e))?;
+
+    log::info!("Connection mode saved successfully");
+    Ok(())
+}
+
+
+#[tauri::command]
+pub async fn is_first_launch(app_handle: AppHandle) -> Result<bool, String> {
+    let store = app_handle
+        .store(STORE_FILE)
+        .map_err(|e| format!("Failed to access store: {}", e))?;
+
+    let setup_completed = store
+        .get(FIRST_LAUNCH_KEY)
+        .and_then(|v| v.as_bool())
+        .unwrap_or(false);
+
+    Ok(!setup_completed)
+}
diff --git a/frontend/src-tauri/src/commands/health.rs b/frontend/src-tauri/src/commands/health.rs
index 394c8462c..e807df7ef 100644
--- a/frontend/src-tauri/src/commands/health.rs
+++ b/frontend/src-tauri/src/commands/health.rs
@@ -1,36 +1,16 @@
-// Command to check if backend is healthy
+use reqwest;
+
 #[tauri::command]
-pub async fn check_backend_health() -> Result<bool, String> {
-    let client = reqwest::Client::builder()
+pub async fn check_backend_health(port: u16) -> Result<bool, String> {
+    let url = format!("http://localhost:{}/api/v1/info/status", port);
+
+    match reqwest::Client::new()
+        .get(&url)
         .timeout(std::time::Duration::from_secs(5))
-        .build()
-        .map_err(|e| format!("Failed to create HTTP client: {}", e))?;
-    
-    match client.get("http://localhost:8080/api/v1/info/status").send().await {
-        Ok(response) => {
-            let status = response.status();
-            if status.is_success() {
-                match response.text().await {
-                    Ok(_body) => {
-                        println!("✅ Backend health check successful");
-                        Ok(true)
-                    }
-                    Err(e) => {
-                        println!("⚠️ Failed to read health response: {}", e);
-                        Ok(false)
-                    }
-                }
-            } else {
-                println!("⚠️ Health check failed with status: {}", status);
-                Ok(false)
-            }
-        }
-        Err(e) => {
-            // Only log connection errors if they're not the common "connection refused" during startup
-            if !e.to_string().contains("connection refused") && !e.to_string().contains("No connection could be made") {
-                println!("❌ Health check error: {}", e);
-            }
-            Ok(false)
-        }
+        .send()
+        .await
+    {
+        Ok(response) => Ok(response.status().is_success()),
+        Err(_) => Ok(false), // Return false instead of error for connection failures
     }
-}
\ No newline at end of file
+}
diff --git a/frontend/src-tauri/src/commands/mod.rs b/frontend/src-tauri/src/commands/mod.rs
index ba9995ba6..ecf2f0a8d 100644
--- a/frontend/src-tauri/src/commands/mod.rs
+++ b/frontend/src-tauri/src/commands/mod.rs
@@ -1,9 +1,25 @@
 pub mod backend;
-pub mod health;
 pub mod files;
+pub mod connection;
+pub mod auth;
 pub mod default_app;
+pub mod health;
 
-pub use backend::{start_backend, cleanup_backend};
-pub use health::check_backend_health;
-pub use files::{get_opened_files, clear_opened_files, add_opened_file};
+pub use backend::{cleanup_backend, get_backend_port, start_backend};
+pub use files::{add_opened_file, clear_opened_files, get_opened_files};
+pub use connection::{
+    get_connection_config,
+    is_first_launch,
+    set_connection_mode,
+};
+pub use auth::{
+    clear_auth_token,
+    clear_user_info,
+    get_auth_token,
+    get_user_info,
+    login,
+    save_auth_token,
+    save_user_info,
+};
 pub use default_app::{is_default_pdf_handler, set_as_default_pdf_handler};
+pub use health::check_backend_health;
diff --git a/frontend/src-tauri/src/lib.rs b/frontend/src-tauri/src/lib.rs
index 969479666..cc8e5b65f 100644
--- a/frontend/src-tauri/src/lib.rs
+++ b/frontend/src-tauri/src/lib.rs
@@ -1,18 +1,31 @@
-use tauri::{RunEvent, WindowEvent, Emitter, Manager};
+use tauri::{Manager, RunEvent, WindowEvent, Emitter};
 
 mod utils;
 mod commands;
+mod state;
 
 use commands::{
-    start_backend,
-    check_backend_health,
-    get_opened_files,
-    clear_opened_files,
-    cleanup_backend,
     add_opened_file,
+    check_backend_health,
+    cleanup_backend,
+    clear_auth_token,
+    clear_opened_files,
+    clear_user_info,
     is_default_pdf_handler,
+    get_auth_token,
+    get_backend_port,
+    get_connection_config,
+    get_opened_files,
+    get_user_info,
+    is_first_launch,
+    login,
+    save_auth_token,
+    save_user_info,
+    set_connection_mode,
     set_as_default_pdf_handler,
+    start_backend,
 };
+use state::connection_state::AppConnectionState;
 use utils::{add_log, get_tauri_logs};
 
 #[cfg_attr(mobile, tauri::mobile_entry_point)]
@@ -20,6 +33,9 @@ pub fn run() {
   tauri::Builder::default()
     .plugin(tauri_plugin_shell::init())
     .plugin(tauri_plugin_fs::init())
+    .plugin(tauri_plugin_http::init())
+    .plugin(tauri_plugin_store::Builder::new().build())
+    .manage(AppConnectionState::default())
     .plugin(tauri_plugin_single_instance::init(|app, args, _cwd| {
       // This callback runs when a second instance tries to start
       add_log(format!("📂 Second instance detected with args: {:?}", args));
@@ -60,12 +76,23 @@ pub fn run() {
     })
     .invoke_handler(tauri::generate_handler![
       start_backend,
-      check_backend_health,
+      get_backend_port,
       get_opened_files,
       clear_opened_files,
       get_tauri_logs,
+      get_connection_config,
+      set_connection_mode,
       is_default_pdf_handler,
       set_as_default_pdf_handler,
+      is_first_launch,
+      check_backend_health,
+      login,
+      save_auth_token,
+      get_auth_token,
+      clear_auth_token,
+      save_user_info,
+      get_user_info,
+      clear_user_info,
     ])
     .build(tauri::generate_context!())
     .expect("error while building tauri application")
diff --git a/frontend/src-tauri/src/state/connection_state.rs b/frontend/src-tauri/src/state/connection_state.rs
new file mode 100644
index 000000000..e6a924956
--- /dev/null
+++ b/frontend/src-tauri/src/state/connection_state.rs
@@ -0,0 +1,45 @@
+use serde::{Deserialize, Serialize};
+use std::sync::Mutex;
+
+#[derive(Debug, Clone, Serialize, Deserialize, PartialEq)]
+#[serde(rename_all = "lowercase")]
+pub enum ConnectionMode {
+    Offline,
+    Server,
+}
+
+#[derive(Debug, Clone, Serialize, Deserialize, PartialEq)]
+#[serde(rename_all = "lowercase")]
+pub enum ServerType {
+    SaaS,
+    SelfHosted,
+}
+
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct ServerConfig {
+    pub url: String,
+    pub server_type: ServerType,
+}
+
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct ConnectionState {
+    pub mode: ConnectionMode,
+    pub server_config: Option<ServerConfig>,
+}
+
+impl Default for ConnectionState {
+    fn default() -> Self {
+        Self {
+            mode: ConnectionMode::Offline,
+            server_config: None,
+        }
+    }
+}
+
+pub struct AppConnectionState(pub Mutex<ConnectionState>);
+
+impl Default for AppConnectionState {
+    fn default() -> Self {
+        Self(Mutex::new(ConnectionState::default()))
+    }
+}
diff --git a/frontend/src-tauri/src/state/mod.rs b/frontend/src-tauri/src/state/mod.rs
new file mode 100644
index 000000000..4b8c86c60
--- /dev/null
+++ b/frontend/src-tauri/src/state/mod.rs
@@ -0,0 +1 @@
+pub mod connection_state;
diff --git a/frontend/src-tauri/tauri.conf.json b/frontend/src-tauri/tauri.conf.json
index a6dffc881..a7c3355d8 100644
--- a/frontend/src-tauri/tauri.conf.json
+++ b/frontend/src-tauri/tauri.conf.json
@@ -51,6 +51,11 @@
         "desktopTemplate": "stirling-pdf.desktop"
       }
     },
+    "windows": {
+      "certificateThumbprint": null,
+      "digestAlgorithm": "sha256",
+      "timestampUrl": "http://timestamp.digicert.com"
+    },
     "macOS": {
       "minimumSystemVersion": "10.15",
       "signingIdentity": null,
diff --git a/frontend/src/core/components/annotation/shared/BaseAnnotationTool.tsx b/frontend/src/core/components/annotation/shared/BaseAnnotationTool.tsx
index c61b61cfd..ea093b5be 100644
--- a/frontend/src/core/components/annotation/shared/BaseAnnotationTool.tsx
+++ b/frontend/src/core/components/annotation/shared/BaseAnnotationTool.tsx
@@ -1,9 +1,10 @@
-import React, { useState } from 'react';
+import React, { useEffect, useState } from 'react';
 import { Stack, Alert, Text } from '@mantine/core';
 import { useTranslation } from 'react-i18next';
 import { DrawingControls } from '@app/components/annotation/shared/DrawingControls';
 import { ColorPicker } from '@app/components/annotation/shared/ColorPicker';
 import { usePDFAnnotation } from '@app/components/annotation/providers/PDFAnnotationProvider';
+import { useSignature } from '@app/contexts/SignatureContext';
 
 export interface AnnotationToolConfig {
   enableDrawing?: boolean;
@@ -32,10 +33,34 @@ export const BaseAnnotationTool: React.FC<BaseAnnotationToolProps> = ({
     undo,
     redo
   } = usePDFAnnotation();
+  const { historyApiRef } = useSignature();
 
   const [selectedColor, setSelectedColor] = useState('#000000');
   const [isColorPickerOpen, setIsColorPickerOpen] = useState(false);
   const [signatureData, setSignatureData] = useState<string | null>(null);
+  const [historyAvailability, setHistoryAvailability] = useState({ canUndo: false, canRedo: false });
+  const historyApiInstance = historyApiRef.current;
+
+  useEffect(() => {
+    if (!historyApiInstance) {
+      setHistoryAvailability({ canUndo: false, canRedo: false });
+      return;
+    }
+
+    const updateAvailability = () => {
+      setHistoryAvailability({
+        canUndo: historyApiInstance.canUndo?.() ?? false,
+        canRedo: historyApiInstance.canRedo?.() ?? false,
+      });
+    };
+
+    const unsubscribe = historyApiInstance.subscribe?.(updateAvailability);
+    updateAvailability();
+
+    return () => {
+      unsubscribe?.();
+    };
+  }, [historyApiInstance]);
 
   const handleSignatureDataChange = (data: string | null) => {
     setSignatureData(data);
@@ -54,6 +79,8 @@ export const BaseAnnotationTool: React.FC<BaseAnnotationToolProps> = ({
       <DrawingControls
         onUndo={undo}
         onRedo={redo}
+        canUndo={historyAvailability.canUndo}
+        canRedo={historyAvailability.canRedo}
         onPlaceSignature={config.showPlaceButton ? handlePlaceSignature : undefined}
         hasSignatureData={!!signatureData}
         disabled={disabled}
@@ -86,4 +113,4 @@ export const BaseAnnotationTool: React.FC<BaseAnnotationToolProps> = ({
       />
     </Stack>
   );
-};
\ No newline at end of file
+};
diff --git a/frontend/src/core/components/annotation/shared/ColorPicker.tsx b/frontend/src/core/components/annotation/shared/ColorPicker.tsx
index 40bb363b4..04ae501bb 100644
--- a/frontend/src/core/components/annotation/shared/ColorPicker.tsx
+++ b/frontend/src/core/components/annotation/shared/ColorPicker.tsx
@@ -1,5 +1,6 @@
 import React from 'react';
 import { Modal, Stack, ColorPicker as MantineColorPicker, Group, Button, ColorSwatch } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
 
 interface ColorPickerProps {
   isOpen: boolean;
@@ -14,13 +15,16 @@ export const ColorPicker: React.FC<ColorPickerProps> = ({
   onClose,
   selectedColor,
   onColorChange,
-  title = "Choose Color"
+  title
 }) => {
+  const { t } = useTranslation();
+  const resolvedTitle = title ?? t('colorPicker.title', 'Choose colour');
+
   return (
     <Modal
       opened={isOpen}
       onClose={onClose}
-      title={title}
+      title={resolvedTitle}
       size="sm"
       centered
     >
@@ -36,7 +40,7 @@ export const ColorPicker: React.FC<ColorPickerProps> = ({
         />
         <Group justify="flex-end">
           <Button onClick={onClose}>
-            Done
+            {t('common.done', 'Done')}
           </Button>
         </Group>
       </Stack>
@@ -64,4 +68,4 @@ export const ColorSwatchButton: React.FC<ColorSwatchButtonProps> = ({
       onClick={onClick}
     />
   );
-};
\ No newline at end of file
+};
diff --git a/frontend/src/core/components/annotation/shared/DrawingCanvas.tsx b/frontend/src/core/components/annotation/shared/DrawingCanvas.tsx
index e8600e0a2..cf13532f1 100644
--- a/frontend/src/core/components/annotation/shared/DrawingCanvas.tsx
+++ b/frontend/src/core/components/annotation/shared/DrawingCanvas.tsx
@@ -1,5 +1,6 @@
-import React, { useRef, useState } from 'react';
-import { Paper, Button, Modal, Stack, Text, Popover, ColorPicker as MantineColorPicker } from '@mantine/core';
+import React, { useEffect, useRef, useState } from 'react';
+import { Paper, Button, Modal, Stack, Text, Group } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
 import { ColorSwatchButton } from '@app/components/annotation/shared/ColorPicker';
 import PenSizeSelector from '@app/components/tools/sign/PenSizeSelector';
 import SignaturePad from 'signature_pad';
@@ -20,6 +21,7 @@ interface DrawingCanvasProps {
   modalWidth?: number;
   modalHeight?: number;
   additionalButtons?: React.ReactNode;
+  initialSignatureData?: string;
 }
 
 export const DrawingCanvas: React.FC<DrawingCanvasProps> = ({
@@ -34,12 +36,14 @@ export const DrawingCanvas: React.FC<DrawingCanvasProps> = ({
   disabled = false,
   width = 400,
   height = 150,
+  initialSignatureData,
 }) => {
+  const { t } = useTranslation();
   const previewCanvasRef = useRef<HTMLCanvasElement>(null);
   const modalCanvasRef = useRef<HTMLCanvasElement>(null);
   const padRef = useRef<SignaturePad | null>(null);
   const [modalOpen, setModalOpen] = useState(false);
-  const [colorPickerOpen, setColorPickerOpen] = useState(false);
+  const [savedSignatureData, setSavedSignatureData] = useState<string | null>(null);
 
   const initPad = (canvas: HTMLCanvasElement) => {
     if (!padRef.current) {
@@ -55,6 +59,18 @@ export const DrawingCanvas: React.FC<DrawingCanvasProps> = ({
         minDistance: 5,
         velocityFilterWeight: 0.7,
       });
+
+      // Restore saved signature data if it exists
+      if (savedSignatureData) {
+        const img = new Image();
+        img.onload = () => {
+          const ctx = canvas.getContext('2d');
+          if (ctx) {
+            ctx.drawImage(img, 0, 0, canvas.width, canvas.height);
+          }
+        };
+        img.src = savedSignatureData;
+      }
     }
   };
 
@@ -104,36 +120,35 @@ export const DrawingCanvas: React.FC<DrawingCanvasProps> = ({
     return trimmedCanvas.toDataURL('image/png');
   };
 
+  const renderPreview = (dataUrl: string) => {
+    const canvas = previewCanvasRef.current;
+    if (!canvas) return;
+    const ctx = canvas.getContext('2d');
+    if (!ctx) return;
+
+    const img = new Image();
+    img.onload = () => {
+      ctx.clearRect(0, 0, canvas.width, canvas.height);
+      const scale = Math.min(canvas.width / img.width, canvas.height / img.height);
+      const scaledWidth = img.width * scale;
+      const scaledHeight = img.height * scale;
+      const x = (canvas.width - scaledWidth) / 2;
+      const y = (canvas.height - scaledHeight) / 2;
+
+      ctx.drawImage(img, x, y, scaledWidth, scaledHeight);
+    };
+    img.src = dataUrl;
+  };
+
   const closeModal = () => {
     if (padRef.current && !padRef.current.isEmpty()) {
       const canvas = modalCanvasRef.current;
       if (canvas) {
         const trimmedPng = trimCanvas(canvas);
+        const untrimmedPng = canvas.toDataURL('image/png');
+        setSavedSignatureData(untrimmedPng); // Save untrimmed for restoration
         onSignatureDataChange(trimmedPng);
-
-        // Update preview canvas with proper aspect ratio
-        const img = new Image();
-        img.onload = () => {
-          if (previewCanvasRef.current) {
-            const ctx = previewCanvasRef.current.getContext('2d');
-            if (ctx) {
-              ctx.clearRect(0, 0, previewCanvasRef.current.width, previewCanvasRef.current.height);
-
-              // Calculate scaling to fit within preview canvas while maintaining aspect ratio
-              const scale = Math.min(
-                previewCanvasRef.current.width / img.width,
-                previewCanvasRef.current.height / img.height
-              );
-              const scaledWidth = img.width * scale;
-              const scaledHeight = img.height * scale;
-              const x = (previewCanvasRef.current.width - scaledWidth) / 2;
-              const y = (previewCanvasRef.current.height - scaledHeight) / 2;
-
-              ctx.drawImage(img, x, y, scaledWidth, scaledHeight);
-            }
-          }
-        };
-        img.src = trimmedPng;
+        renderPreview(trimmedPng);
 
         if (onDrawingComplete) {
           onDrawingComplete();
@@ -157,6 +172,7 @@ export const DrawingCanvas: React.FC<DrawingCanvasProps> = ({
         ctx.clearRect(0, 0, previewCanvasRef.current.width, previewCanvasRef.current.height);
       }
     }
+    setSavedSignatureData(null); // Clear saved signature
     onSignatureDataChange(null);
   };
 
@@ -173,67 +189,73 @@ export const DrawingCanvas: React.FC<DrawingCanvasProps> = ({
     }
   };
 
+  useEffect(() => {
+    updatePenColor(selectedColor);
+  }, [selectedColor]);
+
+  useEffect(() => {
+    updatePenSize(penSize);
+  }, [penSize]);
+
+  useEffect(() => {
+    const canvas = previewCanvasRef.current;
+    if (!canvas) return;
+    const ctx = canvas.getContext('2d');
+    if (!ctx) return;
+
+    if (!initialSignatureData) {
+      ctx.clearRect(0, 0, canvas.width, canvas.height);
+      setSavedSignatureData(null);
+
+      return;
+    }
+
+    renderPreview(initialSignatureData);
+    setSavedSignatureData(initialSignatureData);
+  }, [initialSignatureData]);
+
   return (
     <>
       <Paper withBorder p="md">
         <Stack gap="sm">
-          <Text fw={500}>Draw your signature</Text>
           <PrivateContent>
-            <canvas
-              ref={previewCanvasRef}
-              width={width}
-              height={height}
-              style={{
-                border: '1px solid #ccc',
-                borderRadius: '4px',
-                cursor: disabled ? 'default' : 'pointer',
-                backgroundColor: '#ffffff',
-                width: '100%',
-              }}
-              onClick={disabled ? undefined : openModal}
-            />
+          <Text fw={500}>{t('sign.canvas.heading', 'Draw your signature')}</Text>
+          <canvas
+            ref={previewCanvasRef}
+            width={width}
+            height={height}
+            style={{
+              border: '1px solid #ccc',
+              borderRadius: '4px',
+              cursor: disabled ? 'default' : 'pointer',
+              backgroundColor: '#ffffff',
+              width: '100%',
+            }}
+            onClick={disabled ? undefined : openModal}
+          />
           </PrivateContent>
           <Text size="sm" c="dimmed" ta="center">
-            Click to open drawing canvas
+            {t('sign.canvas.clickToOpen', 'Click to open the drawing canvas')}
           </Text>
         </Stack>
       </Paper>
 
-      <Modal opened={modalOpen} onClose={closeModal} title="Draw Your Signature" size="auto" centered>
+      <Modal opened={modalOpen} onClose={closeModal} title={t('sign.canvas.modalTitle', 'Draw your signature')} size="auto" centered>
         <Stack gap="md">
-          <div style={{ display: 'flex', gap: '20px', alignItems: 'flex-end' }}>
-            <div>
-              <Text size="sm" fw={500} mb="xs">Color</Text>
-              <Popover
-                opened={colorPickerOpen}
-                onChange={setColorPickerOpen}
-                position="bottom-start"
-                withArrow
-                withinPortal={false}
-              >
-                <Popover.Target>
-                  <div>
-                    <ColorSwatchButton
-                      color={selectedColor}
-                      onClick={() => setColorPickerOpen(!colorPickerOpen)}
-                    />
-                  </div>
-                </Popover.Target>
-                <Popover.Dropdown>
-                  <MantineColorPicker
-                    format="hex"
-                    value={selectedColor}
-                    onChange={(color) => {
-                      onColorSwatchClick();
-                      updatePenColor(color);
-                    }}
-                    swatches={['#000000', '#0066cc', '#cc0000', '#cc6600', '#009900', '#6600cc']}
-                  />
-                </Popover.Dropdown>
-              </Popover>
-            </div>
-            <div>
-              <Text size="sm" fw={500} mb="xs">Pen Size</Text>
+          <Group gap="lg" align="flex-end" wrap="wrap">
+            <Stack gap={4} style={{ minWidth: 120 }}>
+              <Text size="sm" fw={500}>
+                {t('sign.canvas.colorLabel', 'Colour')}
+              </Text>
+              <ColorSwatchButton
+                color={selectedColor}
+                onClick={onColorSwatchClick}
+              />
+            </Stack>
+            <Stack gap={4} style={{ minWidth: 120 }}>
+              <Text size="sm" fw={500}>
+                {t('sign.canvas.penSizeLabel', 'Pen size')}
+              </Text>
               <PenSizeSelector
                 value={penSize}
                 inputValue={penSizeInput}
@@ -242,12 +264,12 @@ export const DrawingCanvas: React.FC<DrawingCanvasProps> = ({
                   updatePenSize(size);
                 }}
                 onInputChange={onPenSizeInputChange}
-                placeholder="Size"
+                placeholder={t('sign.canvas.penSizePlaceholder', 'Size')}
                 size="compact-sm"
-                style={{ width: '60px' }}
+                style={{ width: '80px' }}
               />
-            </div>
-          </div>
+            </Stack>
+          </Group>
 
           <PrivateContent>
             <canvas
@@ -262,8 +284,8 @@ export const DrawingCanvas: React.FC<DrawingCanvasProps> = ({
                 touchAction: 'none',
                 backgroundColor: 'white',
                 width: '100%',
-                maxWidth: '800px',
-                height: '400px',
+                maxWidth: '50rem',
+                height: '25rem',
                 cursor: 'crosshair',
               }}
             />
@@ -271,10 +293,10 @@ export const DrawingCanvas: React.FC<DrawingCanvasProps> = ({
 
           <div style={{ display: 'flex', justifyContent: 'space-between' }}>
             <Button variant="subtle" color="red" onClick={clear}>
-              Clear Canvas
+              {t('sign.canvas.clear', 'Clear canvas')}
             </Button>
             <Button onClick={closeModal}>
-              Done
+              {t('common.done', 'Done')}
             </Button>
           </div>
         </Stack>
diff --git a/frontend/src/core/components/annotation/shared/DrawingControls.tsx b/frontend/src/core/components/annotation/shared/DrawingControls.tsx
index 62c7c615f..3c28a594e 100644
--- a/frontend/src/core/components/annotation/shared/DrawingControls.tsx
+++ b/frontend/src/core/components/annotation/shared/DrawingControls.tsx
@@ -1,6 +1,7 @@
 import React from 'react';
-import { Group, Button } from '@mantine/core';
+import { Group, Button, ActionIcon, Tooltip } from '@mantine/core';
 import { useTranslation } from 'react-i18next';
+import { LocalIcon } from '@app/components/shared/LocalIcon';
 
 interface DrawingControlsProps {
   onUndo?: () => void;
@@ -8,8 +9,11 @@ interface DrawingControlsProps {
   onPlaceSignature?: () => void;
   hasSignatureData?: boolean;
   disabled?: boolean;
+  canUndo?: boolean;
+  canRedo?: boolean;
   showPlaceButton?: boolean;
   placeButtonText?: string;
+  additionalControls?: React.ReactNode;
 }
 
 export const DrawingControls: React.FC<DrawingControlsProps> = ({
@@ -18,30 +22,48 @@ export const DrawingControls: React.FC<DrawingControlsProps> = ({
   onPlaceSignature,
   hasSignatureData = false,
   disabled = false,
+  canUndo = true,
+  canRedo = true,
   showPlaceButton = true,
-  placeButtonText = "Update and Place"
+  placeButtonText = "Update and Place",
+  additionalControls,
 }) => {
   const { t } = useTranslation();
+  const undoDisabled = disabled || !canUndo;
+  const redoDisabled = disabled || !canRedo;
 
   return (
-    <Group gap="sm">
-      {/* Undo/Redo Controls */}
-      <Button
-        variant="outline"
-        onClick={onUndo}
-        disabled={disabled}
-        flex={1}
-      >
-        {t('sign.undo', 'Undo')}
-      </Button>
-      <Button
-        variant="outline"
-        onClick={onRedo}
-        disabled={disabled}
-        flex={1}
-      >
-        {t('sign.redo', 'Redo')}
-      </Button>
+    <Group gap="xs" wrap="nowrap" align="center">
+      {onUndo && (
+        <Tooltip label={t('sign.undo', 'Undo')}>
+          <ActionIcon
+            variant="subtle"
+            size="lg"
+            aria-label={t('sign.undo', 'Undo')}
+            onClick={onUndo}
+            disabled={undoDisabled}
+            color={undoDisabled ? 'gray' : 'blue'}
+          >
+            <LocalIcon icon="undo" width={20} height={20} style={{ color: 'currentColor' }} />
+          </ActionIcon>
+        </Tooltip>
+      )}
+      {onRedo && (
+        <Tooltip label={t('sign.redo', 'Redo')}>
+          <ActionIcon
+            variant="subtle"
+            size="lg"
+            aria-label={t('sign.redo', 'Redo')}
+            onClick={onRedo}
+            disabled={redoDisabled}
+            color={redoDisabled ? 'gray' : 'blue'}
+          >
+            <LocalIcon icon="redo" width={20} height={20} style={{ color: 'currentColor' }} />
+          </ActionIcon>
+        </Tooltip>
+      )}
+
+      {additionalControls}
 
       {/* Place Signature Button */}
       {showPlaceButton && onPlaceSignature && (
@@ -50,11 +72,11 @@ export const DrawingControls: React.FC<DrawingControlsProps> = ({
           color="blue"
           onClick={onPlaceSignature}
           disabled={disabled || !hasSignatureData}
-          flex={1}
+          ml="auto"
         >
           {placeButtonText}
         </Button>
       )}
     </Group>
   );
-};
\ No newline at end of file
+};
diff --git a/frontend/src/core/components/annotation/shared/TextInputWithFont.tsx b/frontend/src/core/components/annotation/shared/TextInputWithFont.tsx
index aca7430ce..c700d4d05 100644
--- a/frontend/src/core/components/annotation/shared/TextInputWithFont.tsx
+++ b/frontend/src/core/components/annotation/shared/TextInputWithFont.tsx
@@ -34,12 +34,18 @@ export const TextInputWithFont: React.FC<TextInputWithFontProps> = ({
   const [fontSizeInput, setFontSizeInput] = useState(fontSize.toString());
   const fontSizeCombobox = useCombobox();
   const [isColorPickerOpen, setIsColorPickerOpen] = useState(false);
+  const [colorInput, setColorInput] = useState(textColor);
 
   // Sync font size input with prop changes
   useEffect(() => {
     setFontSizeInput(fontSize.toString());
   }, [fontSize]);
 
+  // Sync color input with prop changes
+  useEffect(() => {
+    setColorInput(textColor);
+  }, [textColor]);
+
   const fontOptions = [
     { value: 'Helvetica', label: 'Helvetica' },
     { value: 'Times-Roman', label: 'Times' },
@@ -50,10 +56,15 @@ export const TextInputWithFont: React.FC<TextInputWithFontProps> = ({
 
   const fontSizeOptions = ['8', '12', '16', '20', '24', '28', '32', '36', '40', '48', '56', '64', '72', '80', '96', '112', '128', '144', '160', '176', '192', '200'];
 
+  // Validate hex color
+  const isValidHexColor = (color: string): boolean => {
+    return /^#[0-9A-Fa-f]{6}$/.test(color);
+  };
+
   return (
     <Stack gap="sm">
       <TextInput
-        label={label || t('sign.text.name', 'Signer Name')}
+        label={label || t('sign.text.name', 'Signer name')}
         placeholder={placeholder || t('sign.text.placeholder', 'Enter your full name')}
         value={text}
         onChange={(e) => onTextChange(e.target.value)}
@@ -63,7 +74,7 @@ export const TextInputWithFont: React.FC<TextInputWithFontProps> = ({
 
       {/* Font Selection */}
       <Select
-        label="Font"
+        label={t('sign.text.fontLabel', 'Font')}
         value={fontFamily}
         onChange={(value) => onFontFamilyChange(value || 'Helvetica')}
         data={fontOptions}
@@ -88,8 +99,8 @@ export const TextInputWithFont: React.FC<TextInputWithFontProps> = ({
         >
           <Combobox.Target>
             <TextInput
-              label="Font Size"
-              placeholder="Type or select font size (8-200)"
+              label={t('sign.text.fontSizeLabel', 'Font size')}
+              placeholder={t('sign.text.fontSizePlaceholder', 'Type or select font size (8-200)')}
               value={fontSizeInput}
               onChange={(event) => {
                 const value = event.currentTarget.value;
@@ -135,14 +146,29 @@ export const TextInputWithFont: React.FC<TextInputWithFontProps> = ({
         {onTextColorChange && (
           <Box>
             <TextInput
-              label="Text Color"
-              value={textColor}
-              readOnly
+              label={t('sign.text.colorLabel', 'Text colour')}
+              value={colorInput}
+              placeholder="#000000"
               disabled={disabled}
-              onClick={() => !disabled && setIsColorPickerOpen(true)}
-              style={{ cursor: disabled ? 'default' : 'pointer' }}
+              onChange={(e) => {
+                const value = e.currentTarget.value;
+                setColorInput(value);
+
+                // Update color if valid hex
+                if (isValidHexColor(value)) {
+                  onTextColorChange(value);
+                }
+              }}
+              onBlur={() => {
+                // Revert to valid color on blur if invalid
+                if (!isValidHexColor(colorInput)) {
+                  setColorInput(textColor);
+                }
+              }}
+              style={{ width: '100%' }}
               rightSection={
                 <Box
+                  onClick={() => !disabled && setIsColorPickerOpen(true)}
                   style={{
                     width: 24,
                     height: 24,
@@ -169,4 +195,4 @@ export const TextInputWithFont: React.FC<TextInputWithFontProps> = ({
       )}
     </Stack>
   );
-};
\ No newline at end of file
+};
diff --git a/frontend/src/core/components/shared/UpdateModal.tsx b/frontend/src/core/components/shared/UpdateModal.tsx
new file mode 100644
index 000000000..937f4426d
--- /dev/null
+++ b/frontend/src/core/components/shared/UpdateModal.tsx
@@ -0,0 +1,415 @@
+import React, { useState, useEffect } from 'react';
+import { Modal, Stack, Text, Badge, Button, Group, Loader, Center, Divider, Box, Collapse } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import { updateService, UpdateSummary, FullUpdateInfo, MachineInfo } from '@app/services/updateService';
+import { Z_INDEX_OVER_CONFIG_MODAL } from '@app/styles/zIndex';
+import WarningAmberIcon from '@mui/icons-material/WarningAmber';
+import InfoOutlinedIcon from '@mui/icons-material/InfoOutlined';
+import OpenInNewIcon from '@mui/icons-material/OpenInNew';
+import DownloadIcon from '@mui/icons-material/Download';
+import ExpandMoreIcon from '@mui/icons-material/ExpandMore';
+import ExpandLessIcon from '@mui/icons-material/ExpandLess';
+
+interface UpdateModalProps {
+  opened: boolean;
+  onClose: () => void;
+  currentVersion: string;
+  updateSummary: UpdateSummary;
+  machineInfo: MachineInfo;
+}
+
+const UpdateModal: React.FC<UpdateModalProps> = ({
+  opened,
+  onClose,
+  currentVersion,
+  updateSummary,
+  machineInfo,
+}) => {
+  const { t } = useTranslation();
+  const [fullUpdateInfo, setFullUpdateInfo] = useState<FullUpdateInfo | null>(null);
+  const [loading, setLoading] = useState(true);
+  const [expandedVersions, setExpandedVersions] = useState<Set<number>>(new Set([0]));
+
+  useEffect(() => {
+    if (opened) {
+      setLoading(true);
+      setExpandedVersions(new Set([0]));
+      updateService.getFullUpdateInfo(currentVersion, machineInfo).then((info) => {
+        setFullUpdateInfo(info);
+        setLoading(false);
+      });
+    }
+  }, [opened, currentVersion, machineInfo]);
+
+  const toggleVersion = (index: number) => {
+    setExpandedVersions((prev) => {
+      const newSet = new Set(prev);
+      if (newSet.has(index)) {
+        newSet.delete(index);
+      } else {
+        newSet.add(index);
+      }
+      return newSet;
+    });
+  };
+
+  const getPriorityColor = (priority: string): string => {
+    switch (priority?.toLowerCase()) {
+      case 'urgent':
+        return 'red';
+      case 'normal':
+        return 'blue';
+      case 'minor':
+        return 'cyan';
+      case 'low':
+        return 'gray';
+      default:
+        return 'gray';
+    }
+  };
+
+  const getPriorityLabel = (priority: string): string => {
+    const key = priority?.toLowerCase();
+    return t(`update.priority.${key}`, priority || 'Normal');
+  };
+
+  const downloadUrl = updateService.getDownloadUrl(machineInfo);
+
+  return (
+    <Modal
+      opened={opened}
+      onClose={onClose}
+      title={
+        <Text fw={600} size="lg">
+          {t('update.modalTitle', 'Update Available')}
+        </Text>
+      }
+      centered
+      size="xl"
+      zIndex={Z_INDEX_OVER_CONFIG_MODAL}
+      styles={{
+        body: {
+          maxHeight: '75vh',
+          overflowY: 'auto',
+        },
+      }}
+    >
+      <Stack gap="lg" pt="md">
+        {/* Version Summary Section */}
+        <Box>
+          <Group justify="space-between" align="flex-start" wrap="nowrap" mb="md">
+            <Stack gap={4} style={{ flex: 1 }}>
+              <Text size="xs" c="dimmed" tt="uppercase" fw={500}>
+                {t('update.current', 'Current Version')}
+              </Text>
+              <Text fw={600} size="xl">
+                {currentVersion}
+              </Text>
+            </Stack>
+
+            <Stack gap={4} style={{ flex: 1 }} ta="center">
+              <Text size="xs" c="dimmed" tt="uppercase" fw={500}>
+                {t('update.priorityLabel', 'Priority')}
+              </Text>
+              <Badge
+                color={getPriorityColor(updateSummary.max_priority)}
+                size="lg"
+                variant="filled"
+                style={{ alignSelf: 'center' }}
+              >
+                {getPriorityLabel(updateSummary.max_priority)}
+              </Badge>
+            </Stack>
+
+            <Stack gap={4} style={{ flex: 1 }} ta="right">
+              <Text size="xs" c="dimmed" tt="uppercase" fw={500}>
+                {t('update.latest', 'Latest Version')}
+              </Text>
+              <Text fw={600} size="xl" c="blue">
+                {updateSummary.latest_version}
+              </Text>
+            </Stack>
+          </Group>
+
+          {updateSummary.latest_stable_version && (
+            <Box
+              style={{
+                background: 'var(--mantine-color-green-0)',
+                padding: '10px 16px',
+                borderRadius: '8px',
+                border: '1px solid var(--mantine-color-green-2)',
+              }}
+            >
+              <Group gap="xs" justify="center">
+                <Text size="sm" fw={500}>
+                  {t('update.latestStable', 'Latest Stable')}:
+                </Text>
+                <Text size="sm" fw={600} c="green">
+                  {updateSummary.latest_stable_version}
+                </Text>
+              </Group>
+            </Box>
+          )}
+        </Box>
+
+        {/* Recommended action */}
+        {updateSummary.recommended_action && (
+          <Box
+            style={{
+              background: 'var(--mantine-color-blue-light)',
+              padding: '12px 16px',
+              borderRadius: '8px',
+              border: '1px solid var(--mantine-color-blue-outline)',
+            }}
+          >
+            <Group gap="xs" wrap="nowrap" align="flex-start">
+              <InfoOutlinedIcon style={{ fontSize: 18, color: 'var(--mantine-color-blue-filled)', marginTop: 2 }} />
+              <Box style={{ flex: 1 }}>
+                <Text size="xs" fw={600} mb={4} tt="uppercase">
+                  {t('update.recommendedAction', 'Recommended Action')}
+                </Text>
+                <Text size="sm">
+                  {updateSummary.recommended_action}
+                </Text>
+              </Box>
+            </Group>
+          </Box>
+        )}
+
+        {/* Breaking changes warning */}
+        {updateSummary.any_breaking && (
+          <Box
+            style={{
+              background: 'var(--mantine-color-orange-light)',
+              padding: '12px 16px',
+              borderRadius: '8px',
+              border: '1px solid var(--mantine-color-orange-outline)',
+            }}
+          >
+            <Group gap="xs" wrap="nowrap" align="flex-start">
+              <WarningAmberIcon style={{ fontSize: 18, color: 'var(--mantine-color-orange-filled)', marginTop: 2 }} />
+              <Box style={{ flex: 1 }}>
+                <Text size="xs" fw={600} mb={4} tt="uppercase">
+                  {t('update.breakingChangesDetected', 'Breaking Changes Detected')}
+                </Text>
+                <Text size="sm">
+                  {t(
+                    'update.breakingChangesMessage',
+                    'Some versions contain breaking changes. Please review the migration guides below before updating.'
+                  )}
+                </Text>
+              </Box>
+            </Group>
+          </Box>
+        )}
+
+        {/* Migration guides */}
+        {updateSummary.migration_guides && updateSummary.migration_guides.length > 0 && (
+          <>
+            <Divider />
+            <Stack gap="xs">
+              <Text fw={600} size="sm" tt="uppercase" c="dimmed">
+                {t('update.migrationGuides', 'Migration Guides')}
+              </Text>
+              {updateSummary.migration_guides.map((guide, idx) => (
+                <Box
+                  key={idx}
+                  style={{
+                    border: '1px solid var(--mantine-color-gray-3)',
+                    padding: '12px 16px',
+                    borderRadius: '8px',
+                    background: 'var(--mantine-color-gray-0)',
+                  }}
+                >
+                  <Group justify="space-between" align="center" wrap="nowrap">
+                    <Box style={{ flex: 1 }}>
+                      <Text fw={600} size="sm">
+                        {t('update.version', 'Version')} {guide.version}
+                      </Text>
+                      <Text size="xs" c="dimmed" mt={4}>
+                        {guide.notes}
+                      </Text>
+                    </Box>
+                    <Button
+                      component="a"
+                      href={guide.url}
+                      target="_blank"
+                      variant="light"
+                      size="xs"
+                      rightSection={<OpenInNewIcon style={{ fontSize: 14 }} />}
+                    >
+                      {t('update.viewGuide', 'View Guide')}
+                    </Button>
+                  </Group>
+                </Box>
+              ))}
+            </Stack>
+          </>
+        )}
+
+        {/* Version details */}
+        <Divider />
+        {loading ? (
+          <Center py="xl">
+            <Stack align="center" gap="sm">
+              <Loader size="md" />
+              <Text size="sm" c="dimmed">
+                {t('update.loadingDetailedInfo', 'Loading detailed information...')}
+              </Text>
+            </Stack>
+          </Center>
+        ) : fullUpdateInfo && fullUpdateInfo.new_versions && fullUpdateInfo.new_versions.length > 0 ? (
+          <Stack gap="xs">
+            <Group justify="space-between" align="center">
+              <Text fw={600} size="sm" tt="uppercase" c="dimmed">
+                {t('update.availableUpdates', 'Available Updates')}
+              </Text>
+              <Badge variant="light" color="gray">
+                {fullUpdateInfo.new_versions.length} {fullUpdateInfo.new_versions.length === 1 ? 'version' : 'versions'}
+              </Badge>
+            </Group>
+            <Stack gap="xs">
+              {fullUpdateInfo.new_versions.map((version, index) => {
+                const isExpanded = expandedVersions.has(index);
+                return (
+                  <Box
+                    key={index}
+                    style={{
+                      border: '1px solid var(--mantine-color-gray-3)',
+                      borderRadius: '8px',
+                      overflow: 'hidden',
+                    }}
+                  >
+                    <Group
+                      justify="space-between"
+                      align="center"
+                      p="md"
+                      style={{
+                        cursor: 'pointer',
+                        background: isExpanded ? 'var(--mantine-color-gray-0)' : 'transparent',
+                        transition: 'background 0.15s ease',
+                      }}
+                      onClick={() => toggleVersion(index)}
+                    >
+                      <Group gap="md" style={{ flex: 1 }}>
+                        <Box>
+                          <Text fw={600} size="sm" c="dimmed" mb={2}>
+                            {t('update.version', 'Version')}
+                          </Text>
+                          <Text fw={700} size="lg">
+                            {version.version}
+                          </Text>
+                        </Box>
+                        <Badge color={getPriorityColor(version.priority)} size="md">
+                          {getPriorityLabel(version.priority)}
+                        </Badge>
+                      </Group>
+                      <Group gap="xs">
+                        <Button
+                          component="a"
+                          href={`https://github.com/Stirling-Tools/Stirling-PDF/releases/tag/v${version.version}`}
+                          target="_blank"
+                          variant="light"
+                          size="xs"
+                          onClick={(e) => e.stopPropagation()}
+                          rightSection={<OpenInNewIcon style={{ fontSize: 14 }} />}
+                        >
+                          {t('update.releaseNotes', 'Release Notes')}
+                        </Button>
+                        {isExpanded ? (
+                          <ExpandLessIcon style={{ fontSize: 20, color: 'var(--mantine-color-gray-6)' }} />
+                        ) : (
+                          <ExpandMoreIcon style={{ fontSize: 20, color: 'var(--mantine-color-gray-6)' }} />
+                        )}
+                      </Group>
+                    </Group>
+
+                    <Collapse in={isExpanded}>
+                      <Box p="md" pt={0} style={{ borderTop: '1px solid var(--mantine-color-gray-2)' }}>
+                        <Stack gap="md" mt="md">
+                          <Box>
+                            <Text fw={600} size="sm" mb={6}>
+                              {version.announcement.title}
+                            </Text>
+                            <Text size="sm" c="dimmed" style={{ lineHeight: 1.6 }}>
+                              {version.announcement.message}
+                            </Text>
+                          </Box>
+
+                          {version.compatibility.breaking_changes && (
+                            <Box
+                              style={{
+                                background: 'var(--mantine-color-orange-light)',
+                                padding: '12px',
+                                borderRadius: '6px',
+                                border: '1px solid var(--mantine-color-orange-outline)',
+                              }}
+                            >
+                              <Group gap="xs" align="flex-start" wrap="nowrap" mb="xs">
+                                <WarningAmberIcon style={{ fontSize: 16, color: 'var(--mantine-color-orange-filled)', marginTop: 2 }} />
+                                <Text size="xs" fw={600} tt="uppercase">
+                                  {t('update.breakingChanges', 'Breaking Changes')}
+                                </Text>
+                              </Group>
+                              <Text size="sm" mb="xs">
+                                {version.compatibility.breaking_description ||
+                                  t('update.breakingChangesDefault', 'This version contains breaking changes.')}
+                              </Text>
+                              {version.compatibility.migration_guide_url && (
+                                <Button
+                                  component="a"
+                                  href={version.compatibility.migration_guide_url}
+                                  target="_blank"
+                                  variant="light"
+                                  color="orange"
+                                  size="xs"
+                                  rightSection={<OpenInNewIcon style={{ fontSize: 14 }} />}
+                                >
+                                  {t('update.migrationGuide', 'Migration Guide')}
+                                </Button>
+                              )}
+                            </Box>
+                          )}
+                        </Stack>
+                      </Box>
+                    </Collapse>
+                  </Box>
+                );
+              })}
+            </Stack>
+          </Stack>
+        ) : null}
+
+        {/* Action buttons */}
+        <Divider />
+        <Group justify="flex-end" gap="sm">
+          <Button variant="default" onClick={onClose}>
+            {t('update.close', 'Close')}
+          </Button>
+          <Button
+            variant="light"
+            component="a"
+            href="https://github.com/Stirling-Tools/Stirling-PDF/releases"
+            target="_blank"
+            rightSection={<OpenInNewIcon style={{ fontSize: 16 }} />}
+          >
+            {t('update.viewAllReleases', 'View All Releases')}
+          </Button>
+          {downloadUrl && (
+            <Button
+              component="a"
+              href={downloadUrl}
+              target="_blank"
+              color="green"
+              leftSection={<DownloadIcon style={{ fontSize: 16 }} />}
+            >
+              {t('update.downloadLatest', 'Download Latest')}
+            </Button>
+          )}
+        </Group>
+      </Stack>
+    </Modal>
+  );
+};
+
+export default UpdateModal;
diff --git a/frontend/src/core/components/shared/config/configSections/GeneralSection.tsx b/frontend/src/core/components/shared/config/configSections/GeneralSection.tsx
index de9994705..e80a1fb07 100644
--- a/frontend/src/core/components/shared/config/configSections/GeneralSection.tsx
+++ b/frontend/src/core/components/shared/config/configSections/GeneralSection.tsx
@@ -1,10 +1,12 @@
 import React, { useState, useEffect } from 'react';
-import { Paper, Stack, Switch, Text, Tooltip, NumberInput, SegmentedControl, Code, Group, Anchor, ActionIcon } from '@mantine/core';
+import { Paper, Stack, Switch, Text, Tooltip, NumberInput, SegmentedControl, Code, Group, Anchor, ActionIcon, Button, Badge, Alert } from '@mantine/core';
 import { useTranslation } from 'react-i18next';
 import { usePreferences } from '@app/contexts/PreferencesContext';
 import { useAppConfig } from '@app/contexts/AppConfigContext';
 import type { ToolPanelMode } from '@app/constants/toolPanel';
 import LocalIcon from '@app/components/shared/LocalIcon';
+import { updateService, UpdateSummary } from '@app/services/updateService';
+import UpdateModal from '@app/components/shared/UpdateModal';
 
 const DEFAULT_AUTO_UNZIP_FILE_LIMIT = 4;
 const BANNER_DISMISSED_KEY = 'stirlingpdf_features_banner_dismissed';
@@ -22,12 +24,44 @@ const GeneralSection: React.FC<GeneralSectionProps> = ({ hideTitle = false }) =>
     // Check localStorage on mount
     return localStorage.getItem(BANNER_DISMISSED_KEY) === 'true';
   });
+  const [updateSummary, setUpdateSummary] = useState<UpdateSummary | null>(null);
+  const [updateModalOpened, setUpdateModalOpened] = useState(false);
+  const [checkingUpdate, setCheckingUpdate] = useState(false);
 
   // Sync local state with preference changes
   useEffect(() => {
     setFileLimitInput(preferences.autoUnzipFileLimit);
   }, [preferences.autoUnzipFileLimit]);
 
+  // Check for updates on mount
+  useEffect(() => {
+    if (config?.appVersion && config?.machineType) {
+      checkForUpdate();
+    }
+  }, [config?.appVersion, config?.machineType]);
+
+  const checkForUpdate = async () => {
+    if (!config?.appVersion || !config?.machineType) {
+      return;
+    }
+
+    setCheckingUpdate(true);
+    const machineInfo = {
+      machineType: config.machineType,
+      activeSecurity: config.activeSecurity ?? false,
+      licenseType: config.license ?? 'NORMAL',
+    };
+
+    const summary = await updateService.getUpdateSummary(config.appVersion, machineInfo);
+    if (summary) {
+      const isNewerVersion = updateService.compareVersions(summary.latest_version, config.appVersion) > 0;
+      if (isNewerVersion) {
+        setUpdateSummary(summary);
+      }
+    }
+    setCheckingUpdate(false);
+  };
+
   // Check if login is disabled
   const loginDisabled = !config?.enableLogin;
 
@@ -170,6 +204,108 @@ const GeneralSection: React.FC<GeneralSectionProps> = ({ hideTitle = false }) =>
           </Tooltip>
         </Stack>
       </Paper>
+
+      {/* Update Check Section */}
+      {config?.appVersion && (
+        <Paper withBorder p="md" radius="md">
+          <Stack gap="md">
+            <div>
+              <Group justify="space-between" align="center">
+                <div>
+                  <Text fw={600} size="sm">
+                    {t('settings.general.updates.title', 'Software Updates')}
+                  </Text>
+                  <Text size="xs" c="dimmed" mt={4}>
+                    {t('settings.general.updates.description', 'Check for updates and view version information')}
+                  </Text>
+                </div>
+                {updateSummary && (
+                  <Badge
+                    color={updateSummary.max_priority === 'urgent' ? 'red' : 'blue'}
+                    variant="filled"
+                  >
+                    {updateSummary.max_priority === 'urgent'
+                      ? t('update.urgentUpdateAvailable', 'Urgent Update')
+                      : t('update.updateAvailable', 'Update Available')}
+                  </Badge>
+                )}
+              </Group>
+            </div>
+
+            <Group justify="space-between" align="center">
+              <div>
+                <Text size="sm" c="dimmed">
+                  {t('settings.general.updates.currentVersion', 'Current Version')}:{' '}
+                  <Text component="span" fw={500}>
+                    {config.appVersion}
+                  </Text>
+                </Text>
+                {updateSummary && (
+                  <Text size="sm" c="dimmed" mt={4}>
+                    {t('settings.general.updates.latestVersion', 'Latest Version')}:{' '}
+                    <Text component="span" fw={500} c="blue">
+                      {updateSummary.latest_version}
+                    </Text>
+                  </Text>
+                )}
+              </div>
+              <Group gap="sm">
+                <Button
+                  size="sm"
+                  variant="default"
+                  onClick={checkForUpdate}
+                  loading={checkingUpdate}
+                  leftSection={<LocalIcon icon="refresh-rounded" width="1rem" height="1rem" />}
+                >
+                  {t('settings.general.updates.checkForUpdates', 'Check for Updates')}
+                </Button>
+                {updateSummary && (
+                  <Button
+                    size="sm"
+                    color={updateSummary.max_priority === 'urgent' ? 'red' : 'blue'}
+                    onClick={() => setUpdateModalOpened(true)}
+                    leftSection={<LocalIcon icon="system-update-rounded" width="1rem" height="1rem" />}
+                  >
+                    {t('settings.general.updates.viewDetails', 'View Details')}
+                  </Button>
+                )}
+              </Group>
+            </Group>
+
+            {updateSummary?.any_breaking && (
+              <Alert
+                color="orange"
+                title={t('update.breakingChangesDetected', 'Breaking Changes Detected')}
+                styles={{
+                  title: { fontWeight: 600 }
+                }}
+              >
+                <Text size="sm">
+                  {t(
+                    'update.breakingChangesMessage',
+                    'Some versions contain breaking changes. Please review the migration guides before updating.'
+                  )}
+                </Text>
+              </Alert>
+            )}
+          </Stack>
+        </Paper>
+      )}
+
+      {/* Update Modal */}
+      {updateSummary && config?.appVersion && config?.machineType && (
+        <UpdateModal
+          opened={updateModalOpened}
+          onClose={() => setUpdateModalOpened(false)}
+          currentVersion={config.appVersion}
+          updateSummary={updateSummary}
+          machineInfo={{
+            machineType: config.machineType,
+            activeSecurity: config.activeSecurity ?? false,
+            licenseType: config.license ?? 'NORMAL',
+          }}
+        />
+      )}
     </Stack>
   );
 };
diff --git a/frontend/src/core/components/tools/sign/SavedSignaturesSection.tsx b/frontend/src/core/components/tools/sign/SavedSignaturesSection.tsx
new file mode 100644
index 000000000..fa665c7f3
--- /dev/null
+++ b/frontend/src/core/components/tools/sign/SavedSignaturesSection.tsx
@@ -0,0 +1,292 @@
+import { useCallback, useEffect, useRef, useState } from 'react';
+import { useTranslation } from 'react-i18next';
+import { ActionIcon, Alert, Badge, Box, Card, Group, Stack, Text, TextInput, Tooltip } from '@mantine/core';
+import { LocalIcon } from '@app/components/shared/LocalIcon';
+import { MAX_SAVED_SIGNATURES, SavedSignature, SavedSignatureType } from '@app/hooks/tools/sign/useSavedSignatures';
+
+interface SavedSignaturesSectionProps {
+  signatures: SavedSignature[];
+  disabled?: boolean;
+  isAtCapacity: boolean;
+  onUseSignature: (signature: SavedSignature) => void;
+  onDeleteSignature: (signature: SavedSignature) => void;
+  onRenameSignature: (id: string, label: string) => void;
+}
+
+const typeBadgeColor: Record<SavedSignatureType, string> = {
+  canvas: 'indigo',
+  image: 'teal',
+  text: 'grape',
+};
+
+export const SavedSignaturesSection = ({
+  signatures,
+  disabled = false,
+  isAtCapacity,
+  onUseSignature,
+  onDeleteSignature,
+  onRenameSignature,
+}: SavedSignaturesSectionProps) => {
+  const { t } = useTranslation();
+  const [labelDrafts, setLabelDrafts] = useState<Record<string, string>>({});
+  const [activeIndex, setActiveIndex] = useState(0);
+  const activeSignature = signatures[activeIndex];
+  const appliedSignatureIdRef = useRef<string | null>(null);
+  const onUseSignatureRef = useRef(onUseSignature);
+
+  useEffect(() => {
+    onUseSignatureRef.current = onUseSignature;
+  }, [onUseSignature]);
+
+  useEffect(() => {
+    setLabelDrafts(prev => {
+      const nextDrafts: Record<string, string> = {};
+      signatures.forEach(sig => {
+        nextDrafts[sig.id] = prev[sig.id] ?? sig.label ?? '';
+      });
+      return nextDrafts;
+    });
+  }, [signatures]);
+
+  useEffect(() => {
+    if (signatures.length === 0) {
+      setActiveIndex(0);
+      return;
+    }
+    setActiveIndex(prev => Math.min(prev, Math.max(signatures.length - 1, 0)));
+  }, [signatures.length]);
+
+  const handleNavigate = useCallback(
+    (direction: 'prev' | 'next') => {
+      setActiveIndex(prev => {
+        if (direction === 'prev') {
+          return Math.max(0, prev - 1);
+        }
+        return Math.min(signatures.length - 1, prev + 1);
+      });
+    },
+    [signatures.length]
+  );
+
+  const renderPreview = (signature: SavedSignature) => {
+    if (signature.type === 'text') {
+      return (
+        <Box
+          component="div"
+          style={{
+            fontFamily: signature.fontFamily,
+            fontSize: `${signature.fontSize}px`,
+            color: signature.textColor,
+            display: 'flex',
+            alignItems: 'center',
+            justifyContent: 'center',
+            height: '120px',
+            borderRadius: '0.5rem',
+            backgroundColor: '#ffffff',
+            padding: '0.5rem',
+            textAlign: 'center',
+            overflow: 'hidden',
+          }}
+        >
+          <Text
+            size="lg"
+            style={{
+              fontFamily: signature.fontFamily,
+              color: signature.textColor,
+              whiteSpace: 'nowrap',
+            }}
+          >
+            {signature.signerName}
+          </Text>
+        </Box>
+      );
+    }
+
+    return (
+      <Box
+        component="div"
+        style={{
+          backgroundColor: '#ffffff',
+          borderRadius: '0.5rem',
+          height: '120px',
+          display: 'flex',
+          alignItems: 'center',
+          justifyContent: 'center',
+          padding: '0.5rem',
+        }}
+      >
+        <Box
+          component="img"
+          src={signature.dataUrl}
+          alt={signature.label}
+          style={{
+            maxWidth: '100%',
+            maxHeight: '100%',
+            objectFit: 'contain',
+          }}
+        />
+      </Box>
+    );
+  };
+
+  const emptyState = (
+    <Card withBorder>
+      <Stack gap="xs">
+        <Text fw={500}>{t('sign.saved.emptyTitle', 'No saved signatures yet')}</Text>
+        <Text size="sm" c="dimmed">
+          {t(
+            'sign.saved.emptyDescription',
+            'Draw, upload, or type a signature above, then use "Save to library" to keep up to {{max}} favourites ready to use.',
+            { max: MAX_SAVED_SIGNATURES }
+          )}
+        </Text>
+      </Stack>
+    </Card>
+  );
+
+  const typeLabel = (type: SavedSignatureType) => {
+    switch (type) {
+      case 'canvas':
+        return t('sign.saved.type.canvas', 'Drawing');
+      case 'image':
+        return t('sign.saved.type.image', 'Upload');
+      case 'text':
+        return t('sign.saved.type.text', 'Text');
+      default:
+        return type;
+    }
+  };
+
+  const handleLabelBlur = (signature: SavedSignature) => {
+    const nextValue = labelDrafts[signature.id]?.trim() ?? '';
+    if (!nextValue || nextValue === signature.label) {
+      setLabelDrafts(prev => ({ ...prev, [signature.id]: signature.label }));
+      return;
+    }
+    onRenameSignature(signature.id, nextValue);
+  };
+
+  const handleLabelChange = (event: React.ChangeEvent<HTMLInputElement>, signature: SavedSignature) => {
+    const { value } = event.currentTarget;
+    setLabelDrafts(prev => ({ ...prev, [signature.id]: value }));
+  };
+
+  const handleLabelKeyDown = (event: React.KeyboardEvent<HTMLInputElement>, signature: SavedSignature) => {
+    if (event.key === 'Enter') {
+      event.currentTarget.blur();
+    }
+    if (event.key === 'Escape') {
+      setLabelDrafts(prev => ({ ...prev, [signature.id]: signature.label }));
+      event.currentTarget.blur();
+    }
+  };
+
+  useEffect(() => {
+    if (!activeSignature || disabled) {
+      appliedSignatureIdRef.current = null;
+      return;
+    }
+
+    if (appliedSignatureIdRef.current === activeSignature.id) {
+      return;
+    }
+
+    appliedSignatureIdRef.current = activeSignature.id;
+    onUseSignatureRef.current(activeSignature);
+  }, [activeSignature, disabled]);
+
+  return (
+    <Stack gap="sm">
+      <Group justify="space-between" align="flex-start">
+        <Stack gap={0}>
+          <Text fw={600} size="md">
+            {t('sign.saved.heading', 'Saved signatures')}
+          </Text>
+          <Text size="sm" c="dimmed">
+            {t('sign.saved.description', 'Reuse saved signatures at any time.')}
+          </Text>
+        </Stack>
+      </Group>
+
+      {isAtCapacity && (
+        <Alert color="yellow" title={t('sign.saved.limitTitle', 'Limit reached')}>
+          <Text size="sm">
+            {t('sign.saved.limitDescription', 'Remove a saved signature before adding new ones (max {{max}}).', {
+              max: MAX_SAVED_SIGNATURES,
+            })}
+          </Text>
+        </Alert>
+      )}
+
+      {signatures.length === 0 ? (
+        emptyState
+      ) : (
+        <Stack gap="xs">
+          <Group justify="space-between" align="center">
+            <Text size="sm" c="dimmed">
+              {t('sign.saved.carouselPosition', '{{current}} of {{total}}', {
+                current: activeIndex + 1,
+                total: signatures.length,
+              })}
+            </Text>
+            <Group gap={4}>
+              <ActionIcon
+                variant="light"
+                aria-label={t('sign.saved.prev', 'Previous')}
+                onClick={() => handleNavigate('prev')}
+                disabled={disabled || activeIndex === 0}
+              >
+                <LocalIcon icon="material-symbols:chevron-left-rounded" width={18} height={18} />
+              </ActionIcon>
+              <ActionIcon
+                variant="light"
+                aria-label={t('sign.saved.next', 'Next')}
+                onClick={() => handleNavigate('next')}
+                disabled={disabled || activeIndex >= signatures.length - 1}
+              >
+                <LocalIcon icon="material-symbols:chevron-right-rounded" width={18} height={18} />
+              </ActionIcon>
+            </Group>
+          </Group>
+
+          {activeSignature && (
+            <Card withBorder padding="sm" key={activeSignature.id}>
+              <Stack gap="sm">
+                <Group justify="space-between" align="center">
+                  <Badge color={typeBadgeColor[activeSignature.type]} variant="light">
+                    {typeLabel(activeSignature.type)}
+                  </Badge>
+                  <Tooltip label={t('sign.saved.delete', 'Remove')}>
+                    <ActionIcon
+                      variant="subtle"
+                      color="red"
+                      aria-label={t('sign.saved.delete', 'Remove')}
+                      onClick={() => onDeleteSignature(activeSignature)}
+                      disabled={disabled}
+                    >
+                      <LocalIcon icon="material-symbols:delete-outline-rounded" width={18} height={18} />
+                    </ActionIcon>
+                  </Tooltip>
+                </Group>
+
+                {renderPreview(activeSignature)}
+
+                <TextInput
+                  label={t('sign.saved.label', 'Label')}
+                  value={labelDrafts[activeSignature.id] ?? activeSignature.label}
+                  onChange={event => handleLabelChange(event, activeSignature)}
+                  onBlur={() => handleLabelBlur(activeSignature)}
+                  onKeyDown={event => handleLabelKeyDown(event, activeSignature)}
+                  disabled={disabled}
+                />
+
+              </Stack>
+            </Card>
+          )}
+        </Stack>
+      )}
+    </Stack>
+  );
+};
+
+export default SavedSignaturesSection;
diff --git a/frontend/src/core/components/tools/sign/SignSettings.tsx b/frontend/src/core/components/tools/sign/SignSettings.tsx
index 09200727d..ea5d237c7 100644
--- a/frontend/src/core/components/tools/sign/SignSettings.tsx
+++ b/frontend/src/core/components/tools/sign/SignSettings.tsx
@@ -1,9 +1,11 @@
-import { useState, useEffect } from 'react';
+import { useState, useEffect, useMemo, useRef, useCallback } from 'react';
 import { useTranslation } from "react-i18next";
-import { Stack, Button, Text, Alert, Tabs, SegmentedControl } from '@mantine/core';
+import { Stack, Button, Text, Alert, SegmentedControl, Divider, ActionIcon, Tooltip, Group, Box } from '@mantine/core';
 import { SignParameters } from "@app/hooks/tools/sign/useSignParameters";
 import { SuggestedToolsSection } from "@app/components/tools/shared/SuggestedToolsSection";
 import { useSignature } from "@app/contexts/SignatureContext";
+import { useViewer } from "@app/contexts/ViewerContext";
+import { PLACEMENT_ACTIVATION_DELAY, FILE_SWITCH_ACTIVATION_DELAY } from '@app/constants/signConstants';
 
 // Import the new reusable components
 import { DrawingCanvas } from "@app/components/annotation/shared/DrawingCanvas";
@@ -11,6 +13,20 @@ import { DrawingControls } from "@app/components/annotation/shared/DrawingContro
 import { ImageUploader } from "@app/components/annotation/shared/ImageUploader";
 import { TextInputWithFont } from "@app/components/annotation/shared/TextInputWithFont";
 import { ColorPicker } from "@app/components/annotation/shared/ColorPicker";
+import { LocalIcon } from "@app/components/shared/LocalIcon";
+import { useSavedSignatures, SavedSignature, SavedSignaturePayload, SavedSignatureType, MAX_SAVED_SIGNATURES, AddSignatureResult } from '@app/hooks/tools/sign/useSavedSignatures';
+import { SavedSignaturesSection } from '@app/components/tools/sign/SavedSignaturesSection';
+
+type SignatureDrafts = {
+  canvas?: string;
+  image?: string;
+  text?: {
+    signerName: string;
+    fontSize: number;
+    fontFamily: string;
+    textColor: string;
+  };
+};
 
 interface SignSettingsProps {
   parameters: SignParameters;
@@ -25,29 +41,323 @@ interface SignSettingsProps {
   onSave?: () => void;
 }
 
+type SignatureSource = 'canvas' | 'image' | 'text' | 'saved';
+
 const SignSettings = ({
   parameters,
   onParameterChange,
   disabled = false,
   onActivateSignaturePlacement,
   onDeactivateSignature,
+  onUpdateDrawSettings,
   onUndo,
   onRedo,
   onSave
 }: SignSettingsProps) => {
   const { t } = useTranslation();
-  const { isPlacementMode } = useSignature();
+  const { isPlacementMode, signaturesApplied, historyApiRef } = useSignature();
+  const { activeFileIndex } = useViewer();
+  const [historyAvailability, setHistoryAvailability] = useState({ canUndo: false, canRedo: false });
+  const historyApiInstance = historyApiRef.current;
 
   // State for drawing
   const [selectedColor, setSelectedColor] = useState('#000000');
   const [penSize, setPenSize] = useState(2);
   const [penSizeInput, setPenSizeInput] = useState('2');
   const [isColorPickerOpen, setIsColorPickerOpen] = useState(false);
-  const [interactionMode, setInteractionMode] = useState<'move' | 'place'>('move');
+  const [isPlacementManuallyPaused, setPlacementManuallyPaused] = useState(false);
 
   // State for different signature types
-  const [canvasSignatureData, setCanvasSignatureData] = useState<string | null>(null);
-  const [imageSignatureData, setImageSignatureData] = useState<string | null>(null);
+  const [canvasSignatureData, setCanvasSignatureData] = useState<string | undefined>();
+  const [imageSignatureData, setImageSignatureData] = useState<string | undefined>();
+  const [signatureDrafts, setSignatureDrafts] = useState<SignatureDrafts>({});
+  const lastSyncedTextDraft = useRef<SignatureDrafts['text'] | null>(null);
+  const lastAppliedPlacementKey = useRef<string | null>(null);
+  const previousFileIndexRef = useRef(activeFileIndex);
+  const {
+    savedSignatures,
+    isAtCapacity: isSavedSignatureLimitReached,
+    addSignature,
+    removeSignature,
+    updateSignatureLabel,
+    byTypeCounts,
+  } = useSavedSignatures();
+  const [signatureSource, setSignatureSource] = useState<SignatureSource>(parameters.signatureType);
+  const [lastSavedSignatureKeys, setLastSavedSignatureKeys] = useState<Record<SavedSignatureType, string | null>>({
+    canvas: null,
+    image: null,
+    text: null,
+  });
+
+  const buildTextSignatureKey = useCallback(
+    (signerName: string, fontSize: number, fontFamily: string, textColor: string) =>
+      JSON.stringify({
+        signerName: signerName.trim(),
+        fontSize,
+        fontFamily,
+        textColor,
+      }),
+    []
+  );
+
+  const getDefaultSavedLabel = useCallback(
+    (type: SavedSignatureType) => {
+      const nextIndex = (byTypeCounts[type] ?? 0) + 1;
+      let baseLabel = t('sign.saved.defaultLabel', 'Signature');
+      if (type === 'canvas') {
+        baseLabel = t('sign.saved.defaultCanvasLabel', 'Drawing signature');
+      } else if (type === 'image') {
+        baseLabel = t('sign.saved.defaultImageLabel', 'Uploaded signature');
+      } else if (type === 'text') {
+        baseLabel = t('sign.saved.defaultTextLabel', 'Typed signature');
+      }
+      return `${baseLabel} ${nextIndex}`;
+    },
+    [byTypeCounts, t]
+  );
+
+  const signatureKeysByType = useMemo(() => {
+    const canvasKey = canvasSignatureData ?? null;
+    const imageKey = imageSignatureData ?? null;
+    const textKey = buildTextSignatureKey(
+      parameters.signerName ?? '',
+      parameters.fontSize ?? 16,
+      parameters.fontFamily ?? 'Helvetica',
+      parameters.textColor ?? '#000000'
+    );
+    return {
+      canvas: canvasKey,
+      image: imageKey,
+      text: textKey,
+    };
+  }, [canvasSignatureData, imageSignatureData, buildTextSignatureKey, parameters.signerName, parameters.fontSize, parameters.fontFamily, parameters.textColor]);
+
+  const saveSignatureToLibrary = useCallback(
+    (payload: SavedSignaturePayload, type: SavedSignatureType): AddSignatureResult => {
+      if (isSavedSignatureLimitReached) {
+        return { success: false, reason: 'limit' };
+      }
+      return addSignature(payload, getDefaultSavedLabel(type));
+    },
+    [addSignature, getDefaultSavedLabel, isSavedSignatureLimitReached]
+  );
+
+  const setLastSavedKeyForType = useCallback(
+    (type: SavedSignatureType, explicitKey?: string | null) => {
+      setLastSavedSignatureKeys(prev => ({
+        ...prev,
+        [type]: explicitKey !== undefined ? explicitKey : signatureKeysByType[type] ?? null,
+      }));
+    },
+    [signatureKeysByType]
+  );
+
+  const handleSaveCanvasSignature = useCallback(() => {
+    if (!canvasSignatureData) {
+      return;
+    }
+    const result = saveSignatureToLibrary({ type: 'canvas', dataUrl: canvasSignatureData }, 'canvas');
+    if (result.success) {
+      setLastSavedKeyForType('canvas');
+    }
+  }, [canvasSignatureData, saveSignatureToLibrary, setLastSavedKeyForType]);
+
+  const handleSaveImageSignature = useCallback(() => {
+    if (!imageSignatureData) {
+      return;
+    }
+    const result = saveSignatureToLibrary({ type: 'image', dataUrl: imageSignatureData }, 'image');
+    if (result.success) {
+      setLastSavedKeyForType('image');
+    }
+  }, [imageSignatureData, saveSignatureToLibrary, setLastSavedKeyForType]);
+
+  const handleSaveTextSignature = useCallback(() => {
+    const signerName = (parameters.signerName ?? '').trim();
+    if (!signerName) {
+      return;
+    }
+    const result = saveSignatureToLibrary(
+      {
+        type: 'text',
+        signerName,
+        fontFamily: parameters.fontFamily ?? 'Helvetica',
+        fontSize: parameters.fontSize ?? 16,
+        textColor: parameters.textColor ?? '#000000',
+      },
+      'text'
+    );
+    if (result.success) {
+      setLastSavedKeyForType('text');
+    }
+  }, [
+    parameters.fontFamily,
+    parameters.fontSize,
+    parameters.signerName,
+    parameters.textColor,
+    saveSignatureToLibrary,
+    setLastSavedKeyForType,
+  ]);
+
+  const handleUseSavedSignature = useCallback(
+    (signature: SavedSignature) => {
+      setPlacementManuallyPaused(false);
+
+      if (signature.type === 'canvas') {
+        if (parameters.signatureType !== 'canvas') {
+          onParameterChange('signatureType', 'canvas');
+        }
+        setCanvasSignatureData(signature.dataUrl);
+      } else if (signature.type === 'image') {
+        if (parameters.signatureType !== 'image') {
+          onParameterChange('signatureType', 'image');
+        }
+        setImageSignatureData(signature.dataUrl);
+      } else if (signature.type === 'text') {
+        if (parameters.signatureType !== 'text') {
+          onParameterChange('signatureType', 'text');
+        }
+        onParameterChange('signerName', signature.signerName);
+        onParameterChange('fontFamily', signature.fontFamily);
+        onParameterChange('fontSize', signature.fontSize);
+        onParameterChange('textColor', signature.textColor);
+      }
+
+      const savedKey =
+        signature.type === 'text'
+          ? buildTextSignatureKey(signature.signerName, signature.fontSize, signature.fontFamily, signature.textColor)
+          : signature.dataUrl;
+      setLastSavedKeyForType(signature.type, savedKey);
+
+      const activate = () => onActivateSignaturePlacement?.();
+      if (typeof window !== 'undefined') {
+        window.setTimeout(activate, PLACEMENT_ACTIVATION_DELAY);
+      } else {
+        activate();
+      }
+    },
+    [
+      buildTextSignatureKey,
+      onActivateSignaturePlacement,
+      onParameterChange,
+      parameters.signatureType,
+      setCanvasSignatureData,
+      setImageSignatureData,
+      setPlacementManuallyPaused,
+      setLastSavedKeyForType,
+    ]
+  );
+
+  const handleDeleteSavedSignature = useCallback(
+    (signature: SavedSignature) => {
+      removeSignature(signature.id);
+    },
+    [removeSignature]
+  );
+
+  const handleRenameSavedSignature = useCallback(
+    (id: string, label: string) => {
+      updateSignatureLabel(id, label);
+    },
+    [updateSignatureLabel]
+  );
+
+  const renderSaveButton = (type: SavedSignatureType, isReady: boolean, onClick: () => void) => {
+    const label = t('sign.saved.saveButton', 'Save signature');
+    const currentKey = signatureKeysByType[type];
+    const lastSavedKey = lastSavedSignatureKeys[type];
+    const hasChanges = Boolean(currentKey && currentKey !== lastSavedKey);
+    const isSaved = isReady && !hasChanges;
+
+    let tooltipMessage: string | undefined;
+    if (!isReady) {
+      tooltipMessage = t('sign.saved.saveUnavailable', 'Create a signature first to save it.');
+    } else if (isSaved) {
+      tooltipMessage = t('sign.saved.noChanges', 'Current signature is already saved.');
+    } else if (isSavedSignatureLimitReached) {
+      tooltipMessage = t('sign.saved.limitDescription', 'Remove a saved signature before adding new ones (max {{max}}).', {
+        max: MAX_SAVED_SIGNATURES,
+      });
+    }
+
+    const button = (
+      <Button
+        size="xs"
+        variant="outline"
+        color={isSaved ? 'green' : undefined}
+        onClick={onClick}
+        disabled={!isReady || disabled || isSavedSignatureLimitReached || !hasChanges}
+        leftSection={<LocalIcon icon="material-symbols:save-rounded" width={16} height={16} />}
+      >
+        {isSaved ? t('sign.saved.status.saved', 'Saved') : label}
+      </Button>
+    );
+
+    if (tooltipMessage) {
+      return (
+        <Tooltip label={tooltipMessage}>
+          <span style={{ display: 'inline-block' }}>{button}</span>
+        </Tooltip>
+      );
+    }
+
+    return button;
+  };
+
+  useEffect(() => {
+    if (signatureSource === 'saved') {
+      return;
+    }
+    if (signatureSource !== parameters.signatureType) {
+      setSignatureSource(parameters.signatureType);
+    }
+  }, [parameters.signatureType, signatureSource]);
+
+  useEffect(() => {
+    if (!disabled) {
+      onUpdateDrawSettings?.(selectedColor, penSize);
+    }
+  }, [selectedColor, penSize, disabled, onUpdateDrawSettings]);
+
+  const handleSignatureSourceChange = useCallback(
+    (value: SignatureSource) => {
+      setSignatureSource(value);
+      if (value === 'saved') {
+        return;
+      }
+      if (parameters.signatureType !== value) {
+        onParameterChange('signatureType', value);
+      }
+    },
+    [onParameterChange, parameters.signatureType]
+  );
+
+  useEffect(() => {
+    if (signaturesApplied) {
+      setPlacementManuallyPaused(false);
+    }
+  }, [signaturesApplied]);
+
+  useEffect(() => {
+    if (!historyApiInstance) {
+      setHistoryAvailability({ canUndo: false, canRedo: false });
+      return;
+    }
+
+    const updateAvailability = () => {
+      setHistoryAvailability({
+        canUndo: historyApiInstance.canUndo?.() ?? false,
+        canRedo: historyApiInstance.canRedo?.() ?? false,
+      });
+    };
+
+    const unsubscribe = historyApiInstance.subscribe?.(updateAvailability);
+    updateAvailability();
+
+    return () => {
+      unsubscribe?.();
+    };
+  }, [historyApiInstance]);
 
   // Handle image upload
   const handleImageChange = async (file: File | null) => {
@@ -66,64 +376,185 @@ const SignSettings = ({
           reader.readAsDataURL(file);
         });
 
-        // Clear any existing canvas signatures when uploading image
-        setCanvasSignatureData(null);
         setImageSignatureData(result);
       } catch (error) {
         console.error('Error reading file:', error);
       }
     } else if (!file) {
-      setImageSignatureData(null);
-      if (onDeactivateSignature) {
-        onDeactivateSignature();
-      }
+      setImageSignatureData(undefined);
+      onDeactivateSignature?.();
     }
   };
 
   // Handle signature data changes
   const handleCanvasSignatureChange = (data: string | null) => {
+    const nextValue = data ?? undefined;
     setCanvasSignatureData(prev => {
-      if (prev === data) return prev; // Prevent unnecessary updates
-      return data;
+      if (prev === nextValue) {
+        return prev;
+      }
+      return nextValue;
     });
-    if (data) {
-      // Clear image data when canvas is used
-      setImageSignatureData(null);
-    }
   };
 
-  // Handle signature mode deactivation when switching types
-  useEffect(() => {
-    if (parameters.signatureType !== 'text' && onDeactivateSignature) {
-      onDeactivateSignature();
-    }
-  }, [parameters.signatureType]);
+  const hasCanvasSignature = useMemo(() => Boolean(canvasSignatureData), [canvasSignatureData]);
+  const hasImageSignature = useMemo(() => Boolean(imageSignatureData), [imageSignatureData]);
+  const hasTextSignature = useMemo(
+    () => Boolean(parameters.signerName && parameters.signerName.trim() !== ''),
+    [parameters.signerName]
+  );
+
+  const hasAnySignature = hasCanvasSignature || hasImageSignature || hasTextSignature;
+
+  const isCurrentTypeReady = useMemo(() => {
+    switch (parameters.signatureType) {
+      case 'canvas':
+        return hasCanvasSignature;
+      case 'image':
+        return hasImageSignature;
+      case 'text':
+        return hasTextSignature;
+      default:
+        return false;
+    }
+  }, [parameters.signatureType, hasCanvasSignature, hasImageSignature, hasTextSignature]);
+
+  const placementSignatureKey = useMemo(() => {
+    if (!isCurrentTypeReady) {
+      return null;
+    }
+    return signatureKeysByType[parameters.signatureType] ?? null;
+  }, [isCurrentTypeReady, parameters.signatureType, signatureKeysByType]);
+
+  const shouldEnablePlacement = useMemo(() => {
+    if (disabled) return false;
+    return isCurrentTypeReady;
+  }, [disabled, isCurrentTypeReady]);
+
+  const shouldAutoActivate = shouldEnablePlacement && !isPlacementManuallyPaused && !signaturesApplied;
 
-  // Handle text signature activation (including fontSize and fontFamily changes)
   useEffect(() => {
-    if (parameters.signatureType === 'text' && parameters.signerName && parameters.signerName.trim() !== '') {
-      if (onActivateSignaturePlacement) {
-        setInteractionMode('place');
-        setTimeout(() => {
-          onActivateSignaturePlacement();
-        }, 100);
+    setSignatureDrafts(prev => {
+      if (canvasSignatureData) {
+        if (prev.canvas === canvasSignatureData) {
+          return prev;
+        }
+        return { ...prev, canvas: canvasSignatureData };
       }
-    } else if (parameters.signatureType === 'text' && (!parameters.signerName || parameters.signerName.trim() === '')) {
-      if (onDeactivateSignature) {
-        setInteractionMode('move');
-        onDeactivateSignature();
+
+      if (prev.canvas !== undefined) {
+        const next = { ...prev };
+        delete next.canvas;
+        return next;
       }
-    }
-  }, [parameters.signatureType, parameters.signerName, parameters.fontSize, parameters.fontFamily, onActivateSignaturePlacement, onDeactivateSignature]);
 
-  // Reset to move mode when placement mode is deactivated
+      return prev;
+    });
+  }, [canvasSignatureData]);
+
   useEffect(() => {
-    if (!isPlacementMode && interactionMode === 'place') {
-      setInteractionMode('move');
-    }
-  }, [isPlacementMode, interactionMode]);
+    setSignatureDrafts(prev => {
+      if (imageSignatureData) {
+        if (prev.image === imageSignatureData) {
+          return prev;
+        }
+        return { ...prev, image: imageSignatureData };
+      }
+
+      if (prev.image !== undefined) {
+        const next = { ...prev };
+        delete next.image;
+        return next;
+      }
+
+      return prev;
+    });
+  }, [imageSignatureData]);
+
+  useEffect(() => {
+    const nextDraft = {
+      signerName: parameters.signerName || '',
+      fontSize: parameters.fontSize || 16,
+      fontFamily: parameters.fontFamily || 'Helvetica',
+      textColor: parameters.textColor || '#000000',
+    };
+
+    setSignatureDrafts(prev => {
+      const prevDraft = prev.text;
+      if (
+        prevDraft &&
+        prevDraft.signerName === nextDraft.signerName &&
+        prevDraft.fontSize === nextDraft.fontSize &&
+        prevDraft.fontFamily === nextDraft.fontFamily &&
+        prevDraft.textColor === nextDraft.textColor
+      ) {
+        return prev;
+      }
+
+      return { ...prev, text: nextDraft };
+    });
+  }, [parameters.signerName, parameters.fontSize, parameters.fontFamily, parameters.textColor]);
+
+  useEffect(() => {
+    if (parameters.signatureType === 'text') {
+      const draft = signatureDrafts.text;
+      if (!draft) {
+        lastSyncedTextDraft.current = null;
+        return;
+      }
+
+      const currentSignerName = parameters.signerName ?? '';
+      const currentFontSize = parameters.fontSize ?? 16;
+      const currentFontFamily = parameters.fontFamily ?? 'Helvetica';
+      const currentTextColor = parameters.textColor ?? '#000000';
+
+      const isSynced =
+        draft.signerName === currentSignerName &&
+        draft.fontSize === currentFontSize &&
+        draft.fontFamily === currentFontFamily &&
+        draft.textColor === currentTextColor;
+
+      if (isSynced) {
+        lastSyncedTextDraft.current = draft;
+        return;
+      }
+
+      const lastSynced = lastSyncedTextDraft.current;
+      const alreadyAttempted =
+        lastSynced &&
+        lastSynced.signerName === draft.signerName &&
+        lastSynced.fontSize === draft.fontSize &&
+        lastSynced.fontFamily === draft.fontFamily &&
+        lastSynced.textColor === draft.textColor;
+
+      if (!alreadyAttempted) {
+        lastSyncedTextDraft.current = draft;
+        if (draft.signerName !== currentSignerName) {
+          onParameterChange('signerName', draft.signerName);
+        }
+        if (draft.fontSize !== currentFontSize) {
+          onParameterChange('fontSize', draft.fontSize);
+        }
+        if (draft.fontFamily !== currentFontFamily) {
+          onParameterChange('fontFamily', draft.fontFamily);
+        }
+        if (draft.textColor !== currentTextColor) {
+          onParameterChange('textColor', draft.textColor);
+        }
+      }
+    } else {
+      lastSyncedTextDraft.current = null;
+    }
+  }, [
+    parameters.signatureType,
+    parameters.signerName,
+    parameters.fontSize,
+    parameters.fontFamily,
+    parameters.textColor,
+    signatureDrafts.text,
+    onParameterChange,
+  ]);
 
-  // Handle signature data updates
   useEffect(() => {
     let newSignatureData: string | undefined = undefined;
 
@@ -133,110 +564,156 @@ const SignSettings = ({
       newSignatureData = canvasSignatureData;
     }
 
-    // Only update if the signature data has actually changed
     if (parameters.signatureData !== newSignatureData) {
       onParameterChange('signatureData', newSignatureData);
     }
-  }, [parameters.signatureType, parameters.signatureData, canvasSignatureData, imageSignatureData]);
+  }, [parameters.signatureType, parameters.signatureData, canvasSignatureData, imageSignatureData, onParameterChange]);
 
-  // Handle image signature activation - activate when image data syncs with parameters
   useEffect(() => {
-    if (parameters.signatureType === 'image' && imageSignatureData && parameters.signatureData === imageSignatureData && onActivateSignaturePlacement) {
-      setInteractionMode('place');
-      setTimeout(() => {
-        onActivateSignaturePlacement();
-      }, 100);
+    if (!shouldEnablePlacement) {
+      if (isPlacementMode) {
+        onDeactivateSignature?.();
+      }
+      if (isPlacementManuallyPaused) {
+        setPlacementManuallyPaused(false);
+      }
+      return;
     }
-  }, [parameters.signatureType, parameters.signatureData, imageSignatureData]);
 
-  // Handle canvas signature activation - activate when canvas data syncs with parameters
+    if (!shouldAutoActivate || isPlacementMode) {
+      return;
+    }
+
+    if (typeof window !== 'undefined') {
+      const timer = window.setTimeout(() => {
+        onActivateSignaturePlacement?.();
+      }, PLACEMENT_ACTIVATION_DELAY);
+      return () => {
+        window.clearTimeout(timer);
+      };
+    }
+
+    onActivateSignaturePlacement?.();
+  }, [
+    shouldEnablePlacement,
+    shouldAutoActivate,
+    isPlacementMode,
+    isPlacementManuallyPaused,
+    onActivateSignaturePlacement,
+    onDeactivateSignature,
+  ]);
+
   useEffect(() => {
-    if (parameters.signatureType === 'canvas' && canvasSignatureData && parameters.signatureData === canvasSignatureData && onActivateSignaturePlacement) {
-      setInteractionMode('place');
-      setTimeout(() => {
-        onActivateSignaturePlacement();
-      }, 100);
+    if (!shouldAutoActivate || !placementSignatureKey) {
+      if (!shouldEnablePlacement || !shouldAutoActivate) {
+        lastAppliedPlacementKey.current = null;
+      }
+      return;
     }
-  }, [parameters.signatureType, parameters.signatureData, canvasSignatureData]);
 
-  // Draw settings are no longer needed since draw mode is removed
+    if (!isPlacementMode) {
+      lastAppliedPlacementKey.current = null;
+      return;
+    }
 
-  return (
-    <Stack gap="md">
-      {/* Signature Type Selection */}
-      <Tabs
-        value={parameters.signatureType}
-        onChange={(value) => onParameterChange('signatureType', value as 'image' | 'text' | 'canvas')}
-      >
-        <Tabs.List grow>
-          <Tabs.Tab value="canvas" style={{ fontSize: '0.8rem' }}>
-            {t('sign.type.canvas', 'Canvas')}
-          </Tabs.Tab>
-          <Tabs.Tab value="image" style={{ fontSize: '0.8rem' }}>
-            {t('sign.type.image', 'Image')}
-          </Tabs.Tab>
-          <Tabs.Tab value="text" style={{ fontSize: '0.8rem' }}>
-            {t('sign.type.text', 'Text')}
-          </Tabs.Tab>
-        </Tabs.List>
-      </Tabs>
+    if (lastAppliedPlacementKey.current === placementSignatureKey) {
+      return;
+    }
 
-      {/* Drawing Controls */}
-      <DrawingControls
-        onUndo={onUndo}
-        onRedo={onRedo}
-        onPlaceSignature={() => {
-          if (onActivateSignaturePlacement) {
-            onActivateSignaturePlacement();
-          }
-        }}
-        hasSignatureData={!!(canvasSignatureData || imageSignatureData || (parameters.signerName && parameters.signerName.trim() !== ''))}
-        disabled={disabled}
-        showPlaceButton={false}
-        placeButtonText={t('sign.updateAndPlace', 'Update and Place')}
-      />
+    const trigger = () => {
+      onActivateSignaturePlacement?.();
+      lastAppliedPlacementKey.current = placementSignatureKey;
+    };
 
-      {/* Signature Creation based on type */}
-      {parameters.signatureType === 'canvas' && (
-        <DrawingCanvas
-          selectedColor={selectedColor}
-          penSize={penSize}
-          penSizeInput={penSizeInput}
-          onColorSwatchClick={() => setIsColorPickerOpen(true)}
-          onPenSizeChange={setPenSize}
-          onPenSizeInputChange={setPenSizeInput}
-          onSignatureDataChange={handleCanvasSignatureChange}
-          onDrawingComplete={() => {
-            if (onActivateSignaturePlacement) {
-              onActivateSignaturePlacement();
-            }
-          }}
+    if (typeof window !== 'undefined') {
+      const timer = window.setTimeout(trigger, PLACEMENT_ACTIVATION_DELAY);
+      return () => {
+        window.clearTimeout(timer);
+      };
+    }
+
+    trigger();
+  }, [placementSignatureKey, shouldAutoActivate, shouldEnablePlacement, isPlacementMode, onActivateSignaturePlacement]);
+  useEffect(() => {
+    if (activeFileIndex === previousFileIndexRef.current) {
+      return;
+    }
+
+    previousFileIndexRef.current = activeFileIndex;
+
+    if (!shouldEnablePlacement || signaturesApplied) {
+      return;
+    }
+
+    setPlacementManuallyPaused(false);
+    lastAppliedPlacementKey.current = null;
+
+    if (typeof window !== 'undefined') {
+      const timer = window.setTimeout(() => {
+        onActivateSignaturePlacement?.();
+      }, FILE_SWITCH_ACTIVATION_DELAY);
+      return () => {
+        window.clearTimeout(timer);
+      };
+    }
+
+    onActivateSignaturePlacement?.();
+  }, [activeFileIndex, shouldEnablePlacement, signaturesApplied, onActivateSignaturePlacement]);
+
+  const renderSignatureBuilder = () => {
+    if (signatureSource === 'saved') {
+      return (
+        <SavedSignaturesSection
+          signatures={savedSignatures}
           disabled={disabled}
-          additionalButtons={
-            <Button
-              onClick={() => {
-                if (onActivateSignaturePlacement) {
-                  onActivateSignaturePlacement();
-                }
-              }}
-              color="blue"
-              variant="filled"
-              disabled={disabled || !canvasSignatureData}
-            >
-              {t('sign.updateAndPlace', 'Update and Place')}
-            </Button>
-          }
+          isAtCapacity={isSavedSignatureLimitReached}
+          onUseSignature={handleUseSavedSignature}
+          onDeleteSignature={handleDeleteSavedSignature}
+          onRenameSignature={handleRenameSavedSignature}
         />
-      )}
+      );
+    }
 
-      {parameters.signatureType === 'image' && (
-        <ImageUploader
-          onImageChange={handleImageChange}
-          disabled={disabled}
-        />
-      )}
+    if (signatureSource === 'canvas') {
+      return (
+        <Stack gap="xs">
+          <DrawingCanvas
+            selectedColor={selectedColor}
+            penSize={penSize}
+            penSizeInput={penSizeInput}
+            onColorSwatchClick={() => setIsColorPickerOpen(true)}
+            onPenSizeChange={setPenSize}
+            onPenSizeInputChange={setPenSizeInput}
+            onSignatureDataChange={handleCanvasSignatureChange}
+            onDrawingComplete={() => {
+              onActivateSignaturePlacement?.();
+            }}
+            disabled={disabled}
+            initialSignatureData={canvasSignatureData}
+          />
+          <Box style={{ alignSelf: 'flex-start', marginTop: '0.4rem' }}>
+            {renderSaveButton('canvas', hasCanvasSignature, handleSaveCanvasSignature)}
+          </Box>
+        </Stack>
+      );
+    }
 
-      {parameters.signatureType === 'text' && (
+    if (signatureSource === 'image') {
+      return (
+        <Stack gap="xs">
+          <ImageUploader
+            onImageChange={handleImageChange}
+            disabled={disabled}
+          />
+          <Box style={{ alignSelf: 'flex-start', marginTop: '0.4rem' }}>
+            {renderSaveButton('image', hasImageSignature, handleSaveImageSignature)}
+          </Box>
+        </Stack>
+      );
+    }
+
+    return (
+      <Stack gap="xs">
         <TextInputWithFont
           text={parameters.signerName || ''}
           onTextChange={(text) => onParameterChange('signerName', text)}
@@ -248,51 +725,195 @@ const SignSettings = ({
           onTextColorChange={(color) => onParameterChange('textColor', color)}
           disabled={disabled}
         />
-      )}
+        <Box style={{ alignSelf: 'flex-start', marginTop: '0.4rem' }}>
+          {renderSaveButton('text', hasTextSignature, handleSaveTextSignature)}
+        </Box>
+      </Stack>
+    );
+  };
 
+  const placementInstructions = () => {
+    if (signatureSource === 'saved') {
+      return t(
+        'sign.instructions.saved',
+        'Select a saved signature above, then click anywhere on the PDF to place it.'
+      );
+    }
+    if (parameters.signatureType === 'canvas') {
+      return t(
+        'sign.instructions.canvas',
+        'After drawing your signature and closing the canvas, click anywhere on the PDF to place it.'
+      );
+    }
+    if (parameters.signatureType === 'image') {
+      return t(
+        'sign.instructions.image',
+        'After uploading your signature image, click anywhere on the PDF to place it.'
+      );
+    }
+    return t(
+      'sign.instructions.text',
+      'After entering your name above, click anywhere on the PDF to place your signature.'
+    );
+  };
 
-      {/* Interaction Mode Toggle */}
-      {(canvasSignatureData || imageSignatureData || (parameters.signerName && parameters.signerName.trim() !== '')) && (
-        <SegmentedControl
-          value={interactionMode}
-          onChange={(value) => {
-            setInteractionMode(value as 'move' | 'place');
-            if (value === 'place') {
-              if (onActivateSignaturePlacement) {
-                onActivateSignaturePlacement();
-              }
-            } else {
-              if (onDeactivateSignature) {
-                onDeactivateSignature();
-              }
-            }
-          }}
-          data={[
-            { label: t('sign.mode.move', 'Move Signature'), value: 'move' },
-            { label: t('sign.mode.place', 'Place Signature'), value: 'place' }
-          ]}
-          fullWidth
-        />
-      )}
+  const placementAlert = isCurrentTypeReady
+    ? {
+        color: isPlacementMode ? 'blue' : 'teal',
+        title: isPlacementMode
+          ? t('sign.instructions.title', 'How to add your signature')
+          : t('sign.instructions.paused', 'Placement paused'),
+        message: isPlacementMode
+          ? placementInstructions()
+          : t('sign.instructions.resumeHint', 'Resume placement to click and add your signature.'),
+      }
+    : {
+        color: 'yellow',
+        title: t('sign.instructions.title', 'How to add your signature'),
+        message: t('sign.instructions.noSignature', 'Create a signature above to enable placement tools.'),
+      };
 
-      {/* Instructions for placing signature */}
-      <Alert color="blue" title={t('sign.instructions.title', 'How to add signature')}>
-        <Text size="sm">
-          {parameters.signatureType === 'canvas' && t('sign.instructions.canvas', 'After drawing your signature in the canvas, close the modal then click anywhere on the PDF to place it.')}
-          {parameters.signatureType === 'image' && t('sign.instructions.image', 'After uploading your signature image above, click anywhere on the PDF to place it.')}
-          {parameters.signatureType === 'text' && t('sign.instructions.text', 'After entering your name above, click anywhere on the PDF to place your signature.')}
+  const handlePausePlacement = () => {
+    setPlacementManuallyPaused(true);
+    onDeactivateSignature?.();
+  };
+
+  const handleResumePlacement = () => {
+    setPlacementManuallyPaused(false);
+    onActivateSignaturePlacement?.();
+  };
+
+  // Handle Escape key to toggle pause/resume
+  useEffect(() => {
+    if (!isCurrentTypeReady) return;
+
+    const handleKeyDown = (e: KeyboardEvent) => {
+      if (e.key === 'Escape') {
+        e.preventDefault();
+        if (isPlacementMode) {
+          handlePausePlacement();
+        } else if (isPlacementManuallyPaused) {
+          handleResumePlacement();
+        }
+      }
+    };
+
+    window.addEventListener('keydown', handleKeyDown);
+    return () => window.removeEventListener('keydown', handleKeyDown);
+  }, [isCurrentTypeReady, isPlacementMode, isPlacementManuallyPaused]);
+
+  const placementToggleControl =
+    onActivateSignaturePlacement || onDeactivateSignature
+      ? isPlacementMode
+        ? (
+            <Tooltip label={t('sign.mode.pause', 'Pause placement')}>
+              <ActionIcon
+                variant="default"
+                size="lg"
+                aria-label={t('sign.mode.pause', 'Pause placement')}
+                onClick={handlePausePlacement}
+                disabled={disabled || !onDeactivateSignature}
+                style={{
+                  width: 'auto',
+                  paddingInline: '0.75rem',
+                  display: 'inline-flex',
+                  alignItems: 'center',
+                  gap: '0.4rem',
+                }}
+              >
+                <LocalIcon icon="material-symbols:pause-rounded" width={20} height={20} />
+                <Text component="span" size="sm" fw={500}>
+                  {t('sign.mode.pause', 'Pause placement')}
+                </Text>
+              </ActionIcon>
+            </Tooltip>
+          )
+        : (
+            <Tooltip label={t('sign.mode.resume', 'Resume placement')}>
+              <ActionIcon
+                variant="default"
+                size="lg"
+                aria-label={t('sign.mode.resume', 'Resume placement')}
+                onClick={handleResumePlacement}
+                disabled={disabled || !isCurrentTypeReady || !onActivateSignaturePlacement}
+                style={{
+                  width: 'auto',
+                  paddingInline: '0.75rem',
+                  display: 'inline-flex',
+                  alignItems: 'center',
+                  gap: '0.4rem',
+                }}
+              >
+                <LocalIcon icon="material-symbols:play-arrow-rounded" width={20} height={20} />
+                <Text component="span" size="sm" fw={500}>
+                  {t('sign.mode.resume', 'Resume placement')}
+                </Text>
+              </ActionIcon>
+            </Tooltip>
+          )
+      : null;
+
+  return (
+    <Stack>
+      <Stack gap="sm">
+        <Text size="sm" c="dimmed">
+          {t('sign.step.createDesc', 'Choose how you want to create the signature')}
         </Text>
-      </Alert>
+        <SegmentedControl
+          value={signatureSource}
+          fullWidth
+          onChange={(value) => handleSignatureSourceChange(value as SignatureSource)}
+          data={[
+            { label: t('sign.type.canvas', 'Draw'), value: 'canvas' },
+            { label: t('sign.type.image', 'Upload'), value: 'image' },
+            { label: t('sign.type.text', 'Type'), value: 'text' },
+            { label: t('sign.type.saved', 'Saved'), value: 'saved' },
+          ]}
+        />
+        {renderSignatureBuilder()}
+      </Stack>
+
+      <Divider />
+
+      <Stack gap="sm">
+        <Text fw={600} size="md">
+          {t('sign.step.place', 'Place & save')}
+        </Text>
+        <Text size="sm" c="dimmed">
+          {t('sign.step.placeDesc', 'Position the signature on your PDF')}
+        </Text>
+
+        <Group gap="xs" wrap="nowrap" align="center">
+          <DrawingControls
+            onUndo={onUndo}
+            onRedo={onRedo}
+            canUndo={historyAvailability.canUndo}
+            canRedo={historyAvailability.canRedo}
+            hasSignatureData={hasAnySignature}
+            disabled={disabled}
+            showPlaceButton={false}
+          />
+          <Box style={{ marginLeft: 'auto' }}>
+            {placementToggleControl}
+          </Box>
+        </Group>
+
+        <Alert color={placementAlert.color} title={placementAlert.title}>
+          <Text size="sm">
+            {placementAlert.message}
+          </Text>
+        </Alert>
+
+      </Stack>
 
-      {/* Color Picker Modal */}
       <ColorPicker
         isOpen={isColorPickerOpen}
         onClose={() => setIsColorPickerOpen(false)}
         selectedColor={selectedColor}
         onColorChange={setSelectedColor}
+        title={t('sign.canvas.colorPickerTitle', 'Choose stroke colour')}
       />
 
-      {/* Apply Signatures Button */}
       {onSave && (
         <Button
           onClick={onSave}
@@ -304,7 +925,6 @@ const SignSettings = ({
         </Button>
       )}
 
-      {/* Suggested Tools Section */}
       <SuggestedToolsSection />
     </Stack>
   );
diff --git a/frontend/src/core/components/viewer/EmbedPdfViewer.tsx b/frontend/src/core/components/viewer/EmbedPdfViewer.tsx
index 7c2c83623..bf9af4eca 100644
--- a/frontend/src/core/components/viewer/EmbedPdfViewer.tsx
+++ b/frontend/src/core/components/viewer/EmbedPdfViewer.tsx
@@ -14,6 +14,7 @@ import { createStirlingFilesAndStubs } from '@app/services/fileStubHelpers';
 import NavigationWarningModal from '@app/components/shared/NavigationWarningModal';
 import { isStirlingFile } from '@app/types/fileContext';
 import { useViewerRightRailButtons } from '@app/components/viewer/useViewerRightRailButtons';
+import { SignaturePlacementOverlay } from '@app/components/viewer/SignaturePlacementOverlay';
 import { useWheelZoom } from '@app/hooks/useWheelZoom';
 
 export interface EmbedPdfViewerProps {
@@ -34,6 +35,7 @@ const EmbedPdfViewerContent = ({
   setActiveFileIndex: externalSetActiveFileIndex,
 }: EmbedPdfViewerProps) => {
   const viewerRef = React.useRef<HTMLDivElement>(null);
+  const pdfContainerRef = useRef<HTMLDivElement>(null);
   const [isViewerHovered, setIsViewerHovered] = React.useState(false);
 
   const { isThumbnailSidebarVisible, toggleThumbnailSidebar, zoomActions, panActions: _panActions, rotationActions: _rotationActions, getScrollState, getRotationState, isAnnotationMode, isAnnotationsVisible, exportActions } = useViewer();
@@ -53,7 +55,7 @@ const EmbedPdfViewerContent = ({
   }, [rotationState.rotation]);
 
   // Get signature context
-  const { signatureApiRef, historyApiRef } = useSignature();
+  const { signatureApiRef, historyApiRef, signatureConfig, isPlacementMode } = useSignature();
 
   // Get current file from FileContext
   const { selectors, state } = useFileState();
@@ -71,6 +73,9 @@ const EmbedPdfViewerContent = ({
 
   // Enable annotations when: in sign mode, OR annotation mode is active, OR we want to show existing annotations
   const shouldEnableAnnotations = isSignatureMode || isAnnotationMode || isAnnotationsVisible;
+  const isPlacementOverlayActive = Boolean(
+    isSignatureMode && shouldEnableAnnotations && isPlacementMode && signatureConfig
+  );
 
   // Track which file tab is active
   const [internalActiveFileIndex, setInternalActiveFileIndex] = useState(0);
@@ -247,15 +252,17 @@ const EmbedPdfViewerContent = ({
       ) : (
         <>
           {/* EmbedPDF Viewer */}
-          <Box style={{
-            position: 'relative',
-            flex: 1,
-            overflow: 'hidden',
-            minHeight: 0,
-            minWidth: 0,
-            marginRight: isThumbnailSidebarVisible ? '15rem' : '0',
-            transition: 'margin-right 0.3s ease'
-          }}>
+          <Box
+            ref={pdfContainerRef}
+            style={{
+              position: 'relative',
+              flex: 1,
+              overflow: 'hidden',
+              minHeight: 0,
+              minWidth: 0,
+              marginRight: isThumbnailSidebarVisible ? '15rem' : '0',
+              transition: 'margin-right 0.3s ease'
+            }}>
             <LocalEmbedPDF
               key={currentFile && isStirlingFile(currentFile) ? currentFile.fileId : (effectiveFile.file instanceof File ? effectiveFile.file.name : effectiveFile.url)}
               file={effectiveFile.file}
@@ -268,6 +275,11 @@ const EmbedPdfViewerContent = ({
                 // Future: Handle signature completion
               }}
             />
+            <SignaturePlacementOverlay
+              containerRef={pdfContainerRef}
+              isActive={isPlacementOverlayActive}
+              signatureConfig={signatureConfig}
+            />
           </Box>
         </>
       )}
diff --git a/frontend/src/core/components/viewer/HistoryAPIBridge.tsx b/frontend/src/core/components/viewer/HistoryAPIBridge.tsx
index bdbf80429..94dca3f6a 100644
--- a/frontend/src/core/components/viewer/HistoryAPIBridge.tsx
+++ b/frontend/src/core/components/viewer/HistoryAPIBridge.tsx
@@ -1,14 +1,16 @@
-import { useImperativeHandle, forwardRef, useEffect } from 'react';
+import { useImperativeHandle, forwardRef, useEffect, useRef } from 'react';
 import { useHistoryCapability } from '@embedpdf/plugin-history/react';
 import { useAnnotationCapability } from '@embedpdf/plugin-annotation/react';
 import { useSignature } from '@app/contexts/SignatureContext';
-import { uuidV4 } from '@embedpdf/models';
+import { PdfAnnotationSubtype, uuidV4 } from '@embedpdf/models';
 import type { HistoryAPI } from '@app/components/viewer/viewerTypes';
+import { ANNOTATION_RECREATION_DELAY_MS, ANNOTATION_VERIFICATION_DELAY_MS } from '@app/constants/app';
 
 export const HistoryAPIBridge = forwardRef<HistoryAPI>(function HistoryAPIBridge(_, ref) {
   const { provides: historyApi } = useHistoryCapability();
   const { provides: annotationApi } = useAnnotationCapability();
   const { getImageData, storeImageData } = useSignature();
+  const restoringIds = useRef<Set<string>>(new Set());
 
   // Monitor annotation events to detect when annotations are restored
   useEffect(() => {
@@ -18,17 +20,58 @@ export const HistoryAPIBridge = forwardRef<HistoryAPI>(function HistoryAPIBridge
       const annotation = event.annotation;
 
       // Store image data for all STAMP annotations immediately when created or modified
-      if (annotation && annotation.type === 13 && annotation.id && annotation.imageSrc) {
+      if (annotation && annotation.type === PdfAnnotationSubtype.STAMP && annotation.id && annotation.imageSrc) {
         const storedImageData = getImageData(annotation.id);
-        if (!storedImageData || storedImageData !== annotation.imageSrc) {
+        if (!storedImageData) {
           storeImageData(annotation.id, annotation.imageSrc);
         }
       }
 
+      if (annotation && annotation.type === PdfAnnotationSubtype.STAMP && annotation.id) {
+        // Prevent infinite loops when we recreate annotations
+        if (restoringIds.current.has(annotation.id)) {
+          restoringIds.current.delete(annotation.id);
+          return;
+        }
+
+        const storedImageData = getImageData(annotation.id);
+        // If EmbedPDF cropped the image (imageSrc changed), recreate annotation using stored data
+        if (storedImageData && annotation.imageSrc && annotation.imageSrc !== storedImageData) {
+          const newId = uuidV4();
+          restoringIds.current.add(newId);
+          storeImageData(newId, storedImageData);
+
+          const pageIndex = event.pageIndex ?? annotation.pageIndex ?? annotation.object?.pageIndex ?? 0;
+          const rect = annotation.rect || annotation.bounds || annotation.rectangle || annotation.position;
+
+          try {
+            annotationApi.deleteAnnotation(pageIndex, annotation.id);
+            setTimeout(() => {
+              annotationApi.createAnnotation(pageIndex, {
+                type: annotation.type,
+                rect,
+                author: annotation.author || 'Digital Signature',
+                subject: annotation.subject || 'Digital Signature',
+                pageIndex,
+                id: newId,
+                created: annotation.created || new Date(),
+                imageSrc: storedImageData,
+                contents: storedImageData,
+                data: storedImageData,
+                appearance: storedImageData,
+              });
+            }, ANNOTATION_RECREATION_DELAY_MS);
+          } catch (restoreError) {
+            console.error('HistoryAPI: Failed to restore cropped signature:', restoreError);
+          }
+          return;
+        }
+      }
+
       // Handle annotation restoration after undo operations
       if (event.type === 'create' && event.committed) {
         // Check if this is a STAMP annotation (signature) that might need image data restoration
-        if (annotation && annotation.type === 13 && annotation.id) {
+        if (annotation && annotation.type === PdfAnnotationSubtype.STAMP && annotation.id) {
           getImageData(annotation.id);
 
           // Delay the check to allow the annotation to be fully created
@@ -61,12 +104,12 @@ export const HistoryAPIBridge = forwardRef<HistoryAPI>(function HistoryAPIBridge
                 // Small delay to ensure deletion completes
                 setTimeout(() => {
                   annotationApi.createAnnotation(event.pageIndex, restoredData);
-                }, 50);
+                }, ANNOTATION_RECREATION_DELAY_MS);
               } catch (error) {
                 console.error('HistoryAPI: Failed to restore annotation:', error);
               }
             }
-          }, 100);
+          }, ANNOTATION_VERIFICATION_DELAY_MS);
         }
       }
     };
@@ -102,6 +145,21 @@ export const HistoryAPIBridge = forwardRef<HistoryAPI>(function HistoryAPIBridge
     canRedo: () => {
       return historyApi ? historyApi.canRedo() : false;
     },
+
+    subscribe: (listener: () => void) => {
+      if (!historyApi?.onHistoryChange) {
+        return () => {};
+      }
+
+      const wrapped = () => listener();
+      const unsubscribe = historyApi.onHistoryChange(wrapped);
+      listener();
+
+      if (typeof unsubscribe === 'function') {
+        return unsubscribe;
+      }
+      return () => {};
+    },
   }), [historyApi]);
 
   return null; // This is a bridge component with no UI
diff --git a/frontend/src/core/components/viewer/PdfViewerToolbar.tsx b/frontend/src/core/components/viewer/PdfViewerToolbar.tsx
index 107967ef9..a2e36d4e2 100644
--- a/frontend/src/core/components/viewer/PdfViewerToolbar.tsx
+++ b/frontend/src/core/components/viewer/PdfViewerToolbar.tsx
@@ -43,23 +43,32 @@ export function PdfViewerToolbar({
 
   // Register for immediate scroll updates and sync with actual scroll state
   useEffect(() => {
-    registerImmediateScrollUpdate((currentPage, _totalPages) => {
+    const unregister = registerImmediateScrollUpdate((currentPage, _totalPages) => {
       setPageInput(currentPage);
     });
     setPageInput(scrollState.currentPage);
-  }, [registerImmediateScrollUpdate]);
+    return () => {
+      unregister?.();
+    };
+  }, [registerImmediateScrollUpdate, scrollState.currentPage]);
 
   // Register for immediate zoom updates and sync with actual zoom state
   useEffect(() => {
-    registerImmediateZoomUpdate(setDisplayZoomPercent);
+    const unregister = registerImmediateZoomUpdate(setDisplayZoomPercent);
     setDisplayZoomPercent(zoomState.zoomPercent || 140);
-  }, [zoomState.zoomPercent, registerImmediateZoomUpdate]);
+    return () => {
+      unregister?.();
+    };
+  }, [registerImmediateZoomUpdate, zoomState.zoomPercent]);
 
   useEffect(() => {
-    registerImmediateSpreadUpdate((_mode, isDual) => {
+    const unregister = registerImmediateSpreadUpdate((_mode, isDual) => {
       setIsDualPageActive(isDual);
     });
     setIsDualPageActive(spreadState.isDualPage);
+    return () => {
+      unregister?.();
+    };
   }, [registerImmediateSpreadUpdate, spreadState.isDualPage]);
 
   const handleZoomOut = () => {
diff --git a/frontend/src/core/components/viewer/SignatureAPIBridge.tsx b/frontend/src/core/components/viewer/SignatureAPIBridge.tsx
index 6eb8d58e0..e66bc60e0 100644
--- a/frontend/src/core/components/viewer/SignatureAPIBridge.tsx
+++ b/frontend/src/core/components/viewer/SignatureAPIBridge.tsx
@@ -1,12 +1,211 @@
-import { useImperativeHandle, forwardRef, useEffect } from 'react';
+import { useImperativeHandle, forwardRef, useEffect, useCallback, useRef, useState } from 'react';
 import { useAnnotationCapability } from '@embedpdf/plugin-annotation/react';
 import { PdfAnnotationSubtype, uuidV4 } from '@embedpdf/models';
 import { useSignature } from '@app/contexts/SignatureContext';
 import type { SignatureAPI } from '@app/components/viewer/viewerTypes';
+import type { SignParameters } from '@app/hooks/tools/sign/useSignParameters';
+import { useViewer } from '@app/contexts/ViewerContext';
+
+// Minimum allowed width/height (in pixels) for a signature image or text stamp.
+// This prevents rendering issues and ensures signatures are always visible and usable.
+const MIN_SIGNATURE_DIMENSION = 12;
+
+// Use 2x oversampling to improve text rendering quality (anti-aliasing) when generating signature images.
+// This provides a good balance between visual fidelity and performance/memory usage.
+const TEXT_OVERSAMPLE_FACTOR = 2;
+
+type TextStampImageResult = {
+  dataUrl: string;
+  pixelWidth: number;
+  pixelHeight: number;
+  displayWidth: number;
+  displayHeight: number;
+};
+
+const extractDataUrl = (value: unknown, depth = 0, visited: Set<unknown> = new Set()): string | undefined => {
+  if (!value || depth > 6) return undefined;
+
+  // Prevent circular references
+  if (typeof value === 'object' && visited.has(value)) {
+    return undefined;
+  }
+
+  if (typeof value === 'string') {
+    return value.startsWith('data:image') ? value : undefined;
+  }
+
+  if (typeof value === 'object') {
+    visited.add(value);
+
+    if (Array.isArray(value)) {
+      for (const entry of value) {
+        const result = extractDataUrl(entry, depth + 1, visited);
+        if (result) return result;
+      }
+    } else {
+      for (const key of Object.keys(value as Record<string, unknown>)) {
+        const result = extractDataUrl((value as Record<string, unknown>)[key], depth + 1, visited);
+        if (result) return result;
+      }
+    }
+  }
+
+  return undefined;
+};
+
+const createTextStampImage = (
+  config: SignParameters,
+  displaySize?: { width: number; height: number } | null
+): TextStampImageResult | null => {
+  const text = (config.signerName ?? '').trim();
+  if (!text) {
+    return null;
+  }
+
+  const fontSize = config.fontSize ?? 16;
+  const fontFamily = config.fontFamily ?? 'Helvetica';
+  const textColor = config.textColor ?? '#000000';
+
+  const paddingX = Math.max(4, Math.round(fontSize * 0.8));
+  const paddingY = Math.max(4, Math.round(fontSize * 0.6));
+
+  const measureCanvas = document.createElement('canvas');
+  const measureCtx = measureCanvas.getContext('2d');
+  if (!measureCtx) {
+    return null;
+  }
+
+  measureCtx.font = `${fontSize}px ${fontFamily}`;
+  const metrics = measureCtx.measureText(text);
+  const textWidth = Math.ceil(metrics.width);
+  const naturalWidth = Math.max(MIN_SIGNATURE_DIMENSION, textWidth + paddingX * 2);
+  const naturalHeight = Math.max(MIN_SIGNATURE_DIMENSION, Math.ceil(fontSize + paddingY * 2));
+
+  const scale =
+    displaySize && naturalWidth > 0 && naturalHeight > 0
+      ? Math.min(displaySize.width / naturalWidth, displaySize.height / naturalHeight)
+      : 1;
+
+  const displayWidth = Math.max(MIN_SIGNATURE_DIMENSION, naturalWidth * scale);
+  const displayHeight = Math.max(MIN_SIGNATURE_DIMENSION, naturalHeight * scale);
+
+  const canvasWidth = Math.max(
+    MIN_SIGNATURE_DIMENSION,
+    Math.round(displayWidth * TEXT_OVERSAMPLE_FACTOR)
+  );
+  const canvasHeight = Math.max(
+    MIN_SIGNATURE_DIMENSION,
+    Math.round(displayHeight * TEXT_OVERSAMPLE_FACTOR)
+  );
+
+  const canvas = document.createElement('canvas');
+  canvas.width = canvasWidth;
+  canvas.height = canvasHeight;
+
+  const ctx = canvas.getContext('2d');
+  if (!ctx) {
+    return null;
+  }
+
+  const effectiveScale = scale * TEXT_OVERSAMPLE_FACTOR;
+  ctx.scale(effectiveScale, effectiveScale);
+
+  ctx.fillStyle = textColor;
+  ctx.font = `${fontSize}px ${fontFamily}`;
+  ctx.textAlign = 'left';
+  ctx.textBaseline = 'middle';
+
+  const horizontalPadding = paddingX;
+  const verticalCenter = naturalHeight / 2;
+  ctx.fillText(text, horizontalPadding, verticalCenter);
+
+  return {
+    dataUrl: canvas.toDataURL('image/png'),
+    pixelWidth: canvasWidth,
+    pixelHeight: canvasHeight,
+    displayWidth,
+    displayHeight,
+  };
+};
 
 export const SignatureAPIBridge = forwardRef<SignatureAPI>(function SignatureAPIBridge(_, ref) {
   const { provides: annotationApi } = useAnnotationCapability();
-  const { signatureConfig, storeImageData, isPlacementMode } = useSignature();
+  const { signatureConfig, storeImageData, isPlacementMode, placementPreviewSize } = useSignature();
+  const { getZoomState, registerImmediateZoomUpdate } = useViewer();
+  const [currentZoom, setCurrentZoom] = useState(() => getZoomState()?.currentZoom ?? 1);
+  const lastStampImageRef = useRef<string | null>(null);
+
+  useEffect(() => {
+    setCurrentZoom(getZoomState()?.currentZoom ?? 1);
+    const unregister = registerImmediateZoomUpdate(percent => {
+      setCurrentZoom(Math.max(percent / 100, 0.01));
+    });
+    return () => {
+      unregister?.();
+    };
+  }, [getZoomState, registerImmediateZoomUpdate]);
+
+  const cssToPdfSize = useCallback(
+    (size: { width: number; height: number }) => {
+      const zoom = currentZoom || 1;
+      const factor = 1 / zoom;
+      return {
+        width: size.width * factor,
+        height: size.height * factor,
+      };
+    },
+    [currentZoom]
+  );
+
+  const applyStampDefaults = useCallback(
+    (imageSrc: string, subject: string, size?: { width: number; height: number }) => {
+      if (!annotationApi) return;
+
+      annotationApi.setActiveTool(null);
+      annotationApi.setActiveTool('stamp');
+      const stampTool = annotationApi.getActiveTool();
+      if (stampTool && stampTool.id === 'stamp') {
+        annotationApi.setToolDefaults('stamp', {
+          imageSrc,
+          subject,
+          ...(size ? { imageSize: { width: size.width, height: size.height } } : {}),
+        });
+      }
+    },
+    [annotationApi]
+  );
+
+  const configureStampDefaults = useCallback(async () => {
+    if (!annotationApi || !signatureConfig) {
+      return;
+    }
+
+    try {
+      if (signatureConfig.signatureType === 'text' && signatureConfig.signerName) {
+        const textStamp = createTextStampImage(signatureConfig, placementPreviewSize);
+        if (textStamp) {
+          const displaySize =
+            placementPreviewSize ?? {
+              width: textStamp.displayWidth,
+              height: textStamp.displayHeight,
+            };
+          const pdfSize = cssToPdfSize(displaySize);
+          lastStampImageRef.current = textStamp.dataUrl;
+          applyStampDefaults(textStamp.dataUrl, `Text Signature - ${signatureConfig.signerName}`, pdfSize);
+        }
+        return;
+      }
+
+      if (signatureConfig.signatureData) {
+        const pdfSize = placementPreviewSize ? cssToPdfSize(placementPreviewSize) : undefined;
+        lastStampImageRef.current = signatureConfig.signatureData;
+        applyStampDefaults(signatureConfig.signatureData, `Digital Signature - ${signatureConfig.reason || 'Document signing'}`, pdfSize);
+        return;
+      }
+    } catch (error) {
+      console.error('Error preparing signature defaults:', error);
+    }
+  }, [annotationApi, signatureConfig, placementPreviewSize, applyStampDefaults, cssToPdfSize]);
 
 
   // Enable keyboard deletion of selected annotations
@@ -108,58 +307,9 @@ export const SignatureAPIBridge = forwardRef<SignatureAPI>(function SignatureAPI
     activateSignaturePlacementMode: () => {
       if (!annotationApi || !signatureConfig) return;
 
-      try {
-        if (signatureConfig.signatureType === 'text' && signatureConfig.signerName) {
-          // Skip native text tools - always use stamp for consistent sizing
-          const activatedTool = null;
-
-          if (!activatedTool) {
-            // Create text image as stamp with actual pixel size matching desired display size
-            const canvas = document.createElement('canvas');
-            const ctx = canvas.getContext('2d');
-            if (ctx) {
-              const baseFontSize = signatureConfig.fontSize || 16;
-              const fontFamily = signatureConfig.fontFamily || 'Helvetica';
-              const textColor = signatureConfig.textColor || '#000000';
-
-              // Canvas pixel size = display size (EmbedPDF uses pixel dimensions directly)
-              canvas.width = Math.max(200, signatureConfig.signerName.length * baseFontSize * 0.6);
-              canvas.height = baseFontSize + 20;
-
-              ctx.fillStyle = textColor;
-              ctx.font = `${baseFontSize}px ${fontFamily}`;
-              ctx.textAlign = 'left';
-              ctx.textBaseline = 'middle';
-              ctx.fillText(signatureConfig.signerName, 10, canvas.height / 2);
-              const dataURL = canvas.toDataURL();
-
-              // Deactivate and reactivate to force refresh
-              annotationApi.setActiveTool(null);
-              annotationApi.setActiveTool('stamp');
-              const stampTool = annotationApi.getActiveTool();
-              if (stampTool && stampTool.id === 'stamp') {
-                annotationApi.setToolDefaults('stamp', {
-                  imageSrc: dataURL,
-                  subject: `Text Signature - ${signatureConfig.signerName}`,
-                });
-              }
-            }
-          }
-        } else if (signatureConfig.signatureData) {
-          // Use stamp tool for image/canvas signatures
-          annotationApi.setActiveTool('stamp');
-          const activeTool = annotationApi.getActiveTool();
-
-          if (activeTool && activeTool.id === 'stamp') {
-            annotationApi.setToolDefaults('stamp', {
-              imageSrc: signatureConfig.signatureData,
-              subject: `Digital Signature - ${signatureConfig.reason || 'Document signing'}`,
-            });
-          }
-        }
-      } catch (error) {
+      configureStampDefaults().catch((error) => {
         console.error('Error activating signature tool:', error);
-      }
+      });
     },
 
     updateDrawSettings: (color: string, size: number) => {
@@ -196,7 +346,7 @@ export const SignatureAPIBridge = forwardRef<SignatureAPI>(function SignatureAPI
       if (pageAnnotationsTask) {
         pageAnnotationsTask.toPromise().then((pageAnnotations: any) => {
           const annotation = pageAnnotations?.find((ann: any) => ann.id === annotationId);
-          if (annotation && annotation.type === 13 && annotation.imageSrc) {
+          if (annotation && annotation.type === PdfAnnotationSubtype.STAMP && annotation.imageSrc) {
             // Store image data before deletion
             storeImageData(annotationId, annotation.imageSrc);
           }
@@ -230,7 +380,61 @@ export const SignatureAPIBridge = forwardRef<SignatureAPI>(function SignatureAPI
         return [];
       }
     },
-  }), [annotationApi, signatureConfig]);
+  }), [annotationApi, signatureConfig, placementPreviewSize, applyStampDefaults]);
+
+  useEffect(() => {
+    if (!annotationApi?.onAnnotationEvent) {
+      return;
+    }
+
+    const unsubscribe = annotationApi.onAnnotationEvent(event => {
+      if (event.type !== 'create' && event.type !== 'update') {
+        return;
+      }
+
+      const annotation: any = event.annotation;
+      const annotationId: string | undefined = annotation?.id;
+      if (!annotationId) {
+        return;
+      }
+
+      const directData =
+        extractDataUrl(annotation.imageSrc) ||
+        extractDataUrl(annotation.imageData) ||
+        extractDataUrl(annotation.appearance) ||
+        extractDataUrl(annotation.stampData) ||
+        extractDataUrl(annotation.contents) ||
+        extractDataUrl(annotation.data) ||
+        extractDataUrl(annotation.customData) ||
+        extractDataUrl(annotation.asset);
+
+      const dataToStore = directData || lastStampImageRef.current;
+      if (dataToStore) {
+        storeImageData(annotationId, dataToStore);
+      }
+    });
+
+    return () => {
+      unsubscribe?.();
+    };
+  }, [annotationApi, storeImageData]);
+
+  useEffect(() => {
+    if (!isPlacementMode) {
+      return;
+    }
+
+    let cancelled = false;
+    configureStampDefaults().catch((error) => {
+      if (!cancelled) {
+        console.error('Error updating signature defaults:', error);
+      }
+    });
+
+    return () => {
+      cancelled = true;
+    };
+  }, [isPlacementMode, configureStampDefaults, placementPreviewSize, signatureConfig]);
 
 
   return null; // This is a bridge component with no UI
diff --git a/frontend/src/core/components/viewer/SignaturePlacementOverlay.tsx b/frontend/src/core/components/viewer/SignaturePlacementOverlay.tsx
new file mode 100644
index 000000000..be5257deb
--- /dev/null
+++ b/frontend/src/core/components/viewer/SignaturePlacementOverlay.tsx
@@ -0,0 +1,171 @@
+import React, { useEffect, useMemo, useState } from 'react';
+import { Box } from '@mantine/core';
+import type { SignParameters } from '@app/hooks/tools/sign/useSignParameters';
+import { buildSignaturePreview, SignaturePreview } from '@app/utils/signaturePreview';
+import { useSignature } from '@app/contexts/SignatureContext';
+import {
+  MAX_PREVIEW_WIDTH_RATIO,
+  MAX_PREVIEW_HEIGHT_RATIO,
+  MAX_PREVIEW_WIDTH_REM,
+  MAX_PREVIEW_HEIGHT_REM,
+  MIN_SIGNATURE_DIMENSION_REM,
+  OVERLAY_EDGE_PADDING_REM,
+} from '@app/constants/signConstants';
+
+// Convert rem to pixels using browser's base font size (typically 16px)
+const remToPx = (rem: number) => rem * parseFloat(getComputedStyle(document.documentElement).fontSize);
+
+interface SignaturePlacementOverlayProps {
+  containerRef: React.RefObject<HTMLElement | null>;
+  isActive: boolean;
+  signatureConfig: SignParameters | null;
+}
+
+export const SignaturePlacementOverlay: React.FC<SignaturePlacementOverlayProps> = ({
+  containerRef,
+  isActive,
+  signatureConfig,
+}) => {
+  const [preview, setPreview] = useState<SignaturePreview | null>(null);
+  const [cursor, setCursor] = useState<{ x: number; y: number } | null>(null);
+  const { setPlacementPreviewSize } = useSignature();
+
+  useEffect(() => {
+    let cancelled = false;
+
+    const buildPreview = async () => {
+      try {
+        const value = await buildSignaturePreview(signatureConfig ?? null);
+        if (!cancelled) {
+          setPreview(value);
+        }
+      } catch (error) {
+        console.error('Failed to build signature preview:', error);
+        if (!cancelled) {
+          setPreview(null);
+        }
+      }
+    };
+
+    buildPreview();
+
+    return () => {
+      cancelled = true;
+    };
+  }, [signatureConfig]);
+
+  useEffect(() => {
+    const element = containerRef.current;
+    if (!isActive || !element) {
+      setCursor(null);
+      return;
+    }
+
+    const handleMove = (event: MouseEvent) => {
+      const rect = element.getBoundingClientRect();
+      setCursor({
+        x: event.clientX - rect.left,
+        y: event.clientY - rect.top,
+      });
+    };
+
+    const handleLeave = () => setCursor(null);
+
+    element.addEventListener('mousemove', handleMove);
+    element.addEventListener('mouseleave', handleLeave);
+
+    return () => {
+      element.removeEventListener('mousemove', handleMove);
+      element.removeEventListener('mouseleave', handleLeave);
+    };
+  }, [containerRef, isActive]);
+
+  const scaledSize = useMemo(() => {
+    if (!preview || !containerRef.current) {
+      return null;
+    }
+
+    const container = containerRef.current;
+    const containerWidth = container.clientWidth || 1;
+    const containerHeight = container.clientHeight || 1;
+
+    const maxWidth = Math.min(containerWidth * MAX_PREVIEW_WIDTH_RATIO, remToPx(MAX_PREVIEW_WIDTH_REM));
+    const maxHeight = Math.min(containerHeight * MAX_PREVIEW_HEIGHT_RATIO, remToPx(MAX_PREVIEW_HEIGHT_REM));
+
+    const scale = Math.min(
+      1,
+      maxWidth / Math.max(preview.width, 1),
+      maxHeight / Math.max(preview.height, 1)
+    );
+
+    return {
+      width: Math.max(remToPx(MIN_SIGNATURE_DIMENSION_REM), preview.width * scale),
+      height: Math.max(remToPx(MIN_SIGNATURE_DIMENSION_REM), preview.height * scale),
+    };
+  }, [preview, containerRef]);
+
+  useEffect(() => {
+    if (!isActive || !scaledSize) {
+      setPlacementPreviewSize(null);
+    } else {
+      setPlacementPreviewSize(scaledSize);
+    }
+  }, [isActive, scaledSize, setPlacementPreviewSize]);
+
+  useEffect(() => {
+    return () => {
+      setPlacementPreviewSize(null);
+    };
+  }, [setPlacementPreviewSize]);
+
+  const display = useMemo(() => {
+    if (!preview || !scaledSize || !cursor || !containerRef.current) {
+      return null;
+    }
+
+    const container = containerRef.current;
+    const containerWidth = container.clientWidth || 1;
+    const containerHeight = container.clientHeight || 1;
+
+    const width = scaledSize.width;
+    const height = scaledSize.height;
+    const edgePadding = remToPx(OVERLAY_EDGE_PADDING_REM);
+
+    const clampedLeft = Math.max(edgePadding, Math.min(cursor.x - width / 2, containerWidth - width - edgePadding));
+    const clampedTop = Math.max(edgePadding, Math.min(cursor.y - height / 2, containerHeight - height - edgePadding));
+
+    return {
+      left: clampedLeft,
+      top: clampedTop,
+      width,
+      height,
+      dataUrl: preview.dataUrl,
+    };
+  }, [preview, scaledSize, cursor, containerRef]);
+
+  if (!isActive || !display || !preview) {
+    return null;
+  }
+
+  return (
+    <Box
+      style={{
+        position: 'absolute',
+        pointerEvents: 'none',
+        left: `${display.left}px`,
+        top: `${display.top}px`,
+        width: `${display.width}px`,
+        height: `${display.height}px`,
+        backgroundImage: `url(${display.dataUrl})`,
+        backgroundSize: '100% 100%',
+        backgroundRepeat: 'no-repeat',
+        backgroundPosition: 'center',
+        boxShadow: '0 0 0 1px rgba(30, 136, 229, 0.55), 0 6px 18px rgba(30, 136, 229, 0.25)',
+        borderRadius: '4px',
+        transition: 'transform 70ms ease-out',
+        transform: 'translateZ(0)',
+        opacity: 0.6,
+      }}
+    />
+  );
+};
diff --git a/frontend/src/core/components/viewer/ZoomAPIBridge.tsx b/frontend/src/core/components/viewer/ZoomAPIBridge.tsx
index b603480d8..80f587870 100644
--- a/frontend/src/core/components/viewer/ZoomAPIBridge.tsx
+++ b/frontend/src/core/components/viewer/ZoomAPIBridge.tsx
@@ -214,4 +214,4 @@ export function ZoomAPIBridge() {
   }, [zoom, zoomState, registerBridge, triggerImmediateZoomUpdate]);
 
   return null;
-}
+}
\ No newline at end of file
diff --git a/frontend/src/core/components/viewer/viewerTypes.ts b/frontend/src/core/components/viewer/viewerTypes.ts
index f8149dce7..3d61377c7 100644
--- a/frontend/src/core/components/viewer/viewerTypes.ts
+++ b/frontend/src/core/components/viewer/viewerTypes.ts
@@ -21,4 +21,5 @@ export interface HistoryAPI {
   redo: () => void;
   canUndo: () => boolean;
   canRedo: () => boolean;
+  subscribe?: (listener: () => void) => () => void;
 }
diff --git a/frontend/src/core/constants/app.ts b/frontend/src/core/constants/app.ts
index c61302c84..04057fa37 100644
--- a/frontend/src/core/constants/app.ts
+++ b/frontend/src/core/constants/app.ts
@@ -3,6 +3,11 @@
 // When no subpath, use empty string instead of '.' to avoid relative path issues
 export const BASE_PATH = (import.meta.env.BASE_URL || '/').replace(/\/$/, '').replace(/^\.$/, '');
 
+// EmbedPDF needs time to remove annotations internally before a recreation runs.
+// Without the buffer we occasionally end up with duplicate annotations or stale image data.
+export const ANNOTATION_RECREATION_DELAY_MS = 50;
+export const ANNOTATION_VERIFICATION_DELAY_MS = 100;
+
 /** For in-app navigations when you must touch window.location (rare). */
 export const withBasePath = (path: string): string => {
   const clean = path.startsWith('/') ? path : `/${path}`;
diff --git a/frontend/src/core/constants/signConstants.ts b/frontend/src/core/constants/signConstants.ts
new file mode 100644
index 000000000..ade726a6c
--- /dev/null
+++ b/frontend/src/core/constants/signConstants.ts
@@ -0,0 +1,15 @@
+// Timeout delays (ms) to allow PDF viewer to complete rendering before activating placement mode
+export const PLACEMENT_ACTIVATION_DELAY = 60;  // Standard delay for signature changes
+export const FILE_SWITCH_ACTIVATION_DELAY = 80; // Slightly longer delay when switching files
+
+// Signature preview sizing
+export const MAX_PREVIEW_WIDTH_RATIO = 0.35;   // Max preview width as percentage of container
+export const MAX_PREVIEW_HEIGHT_RATIO = 0.35;  // Max preview height as percentage of container
+export const MAX_PREVIEW_WIDTH_REM = 15;       // Absolute max width in rem
+export const MAX_PREVIEW_HEIGHT_REM = 10;      // Absolute max height in rem
+export const MIN_SIGNATURE_DIMENSION_REM = 0.75; // Min dimension for visibility
+export const OVERLAY_EDGE_PADDING_REM = 0.25;  // Padding from container edges
+
+// Text signature padding (relative to font size)
+export const HORIZONTAL_PADDING_RATIO = 0.8;
+export const VERTICAL_PADDING_RATIO = 0.6;
diff --git a/frontend/src/core/contexts/AppConfigContext.tsx b/frontend/src/core/contexts/AppConfigContext.tsx
index ad47b415b..2f672da26 100644
--- a/frontend/src/core/contexts/AppConfigContext.tsx
+++ b/frontend/src/core/contexts/AppConfigContext.tsx
@@ -39,6 +39,9 @@ export interface AppConfig {
   license?: string;
   SSOAutoLogin?: boolean;
   serverCertificateEnabled?: boolean;
+  appVersion?: string;
+  machineType?: string;
+  activeSecurity?: boolean;
   error?: string;
 }
 
diff --git a/frontend/src/core/contexts/SignatureContext.tsx b/frontend/src/core/contexts/SignatureContext.tsx
index 753a52414..2912bbaee 100644
--- a/frontend/src/core/contexts/SignatureContext.tsx
+++ b/frontend/src/core/contexts/SignatureContext.tsx
@@ -10,6 +10,8 @@ interface SignatureState {
   isPlacementMode: boolean;
   // Whether signatures have been applied (allows export)
   signaturesApplied: boolean;
+  // Size (in screen units) we want newly placed signatures to use
+  placementPreviewSize: { width: number; height: number } | null;
 }
 
 // Signature actions interface
@@ -26,6 +28,7 @@ interface SignatureActions {
   storeImageData: (id: string, data: string) => void;
   getImageData: (id: string) => string | undefined;
   setSignaturesApplied: (applied: boolean) => void;
+  setPlacementPreviewSize: (size: { width: number; height: number } | null) => void;
 }
 
 // Combined context interface
@@ -42,6 +45,7 @@ const initialState: SignatureState = {
   signatureConfig: null,
   isPlacementMode: false,
   signaturesApplied: true, // Start as true (no signatures placed yet)
+  placementPreviewSize: null,
 };
 
 // Provider component
@@ -131,6 +135,27 @@ export const SignatureProvider: React.FC<{ children: ReactNode }> = ({ children
     }));
   }, []);
 
+  const setPlacementPreviewSize = useCallback((size: { width: number; height: number } | null) => {
+    setState(prev => {
+      const prevSize = prev.placementPreviewSize;
+      const same =
+        (prevSize === null && size === null) ||
+        (prevSize !== null &&
+          size !== null &&
+          Math.abs(prevSize.width - size.width) < 0.5 &&
+          Math.abs(prevSize.height - size.height) < 0.5);
+
+      if (same) {
+        return prev;
+      }
+
+      return {
+        ...prev,
+        placementPreviewSize: size,
+      };
+    });
+  }, []);
+
   // No auto-activation - all modes use manual buttons
 
   const contextValue: SignatureContextValue = {
@@ -149,6 +174,7 @@ export const SignatureProvider: React.FC<{ children: ReactNode }> = ({ children
     storeImageData,
     getImageData,
     setSignaturesApplied,
+    setPlacementPreviewSize,
   };
 
   return (
diff --git a/frontend/src/core/contexts/ViewerContext.tsx b/frontend/src/core/contexts/ViewerContext.tsx
index 2ffe2210d..fc0f1ab70 100644
--- a/frontend/src/core/contexts/ViewerContext.tsx
+++ b/frontend/src/core/contexts/ViewerContext.tsx
@@ -39,14 +39,23 @@ import {
 import { SpreadMode } from '@embedpdf/plugin-spread/react';
 
 function useImmediateNotifier<Args extends unknown[]>() {
-  const callbackRef = useRef<((...args: Args) => void) | null>(null);
+  const callbacksRef = useRef(new Set<(...args: Args) => void>());
 
   const register = useCallback((callback: (...args: Args) => void) => {
-    callbackRef.current = callback;
+    callbacksRef.current.add(callback);
+    return () => {
+      callbacksRef.current.delete(callback);
+    };
   }, []);
 
   const trigger = useCallback((...args: Args) => {
-    callbackRef.current?.(...args);
+    callbacksRef.current.forEach(cb => {
+      try {
+        cb(...args);
+      } catch (error) {
+        console.error('Immediate callback error:', error);
+      }
+    });
   }, []);
 
   return { register, trigger };
@@ -91,9 +100,9 @@ interface ViewerContextType {
   getExportState: () => ExportState;
 
   // Immediate update callbacks
-  registerImmediateZoomUpdate: (callback: (percent: number) => void) => void;
-  registerImmediateScrollUpdate: (callback: (currentPage: number, totalPages: number) => void) => void;
-  registerImmediateSpreadUpdate: (callback: (mode: SpreadMode, isDualPage: boolean) => void) => void;
+  registerImmediateZoomUpdate: (callback: (percent: number) => void) => () => void;
+  registerImmediateScrollUpdate: (callback: (currentPage: number, totalPages: number) => void) => () => void;
+  registerImmediateSpreadUpdate: (callback: (mode: SpreadMode, isDualPage: boolean) => void) => () => void;
 
   // Internal - for bridges to trigger immediate updates
   triggerImmediateScrollUpdate: (currentPage: number, totalPages: number) => void;
diff --git a/frontend/src/core/hooks/tools/showJS/useShowJSOperation.ts b/frontend/src/core/hooks/tools/showJS/useShowJSOperation.ts
index 081fc2723..834402d5f 100644
--- a/frontend/src/core/hooks/tools/showJS/useShowJSOperation.ts
+++ b/frontend/src/core/hooks/tools/showJS/useShowJSOperation.ts
@@ -5,7 +5,6 @@ import type { ToolOperationHook } from '@app/hooks/tools/shared/useToolOperation
 import type { StirlingFile } from '@app/types/fileContext';
 import { extractErrorMessage } from '@app/utils/toolErrorHandler';
 import type { ShowJSParameters } from '@app/hooks/tools/showJS/useShowJSParameters';
-import type { ResponseType } from 'axios';
 
 export interface ShowJSOperationHook extends ToolOperationHook<ShowJSParameters> {
 	scriptText: string | null;
@@ -71,8 +70,7 @@ export const useShowJSOperation = (): ShowJSOperationHook => {
 
 				const response = await apiClient.post('/api/v1/misc/show-javascript', formData, {
 					headers: { 'Content-Type': 'multipart/form-data' },
-					responseType: 'text' as ResponseType,
-					transformResponse: [(data) => data],
+					responseType: 'text',
 				});
 
 				const text: string = typeof response.data === 'string' ? response.data : '';
diff --git a/frontend/src/core/hooks/tools/sign/useSavedSignatures.ts b/frontend/src/core/hooks/tools/sign/useSavedSignatures.ts
new file mode 100644
index 000000000..85ed04ad6
--- /dev/null
+++ b/frontend/src/core/hooks/tools/sign/useSavedSignatures.ts
@@ -0,0 +1,212 @@
+import { useCallback, useEffect, useMemo, useState } from 'react';
+
+const STORAGE_KEY = 'stirling:saved-signatures:v1';
+export const MAX_SAVED_SIGNATURES = 10;
+
+export type SavedSignatureType = 'canvas' | 'image' | 'text';
+
+export type SavedSignaturePayload =
+  | {
+      type: 'canvas';
+      dataUrl: string;
+    }
+  | {
+      type: 'image';
+      dataUrl: string;
+    }
+  | {
+      type: 'text';
+      signerName: string;
+      fontFamily: string;
+      fontSize: number;
+      textColor: string;
+    };
+
+export type SavedSignature = SavedSignaturePayload & {
+  id: string;
+  label: string;
+  createdAt: number;
+  updatedAt: number;
+};
+
+export type AddSignatureResult =
+  | { success: true; signature: SavedSignature }
+  | { success: false; reason: 'limit' | 'invalid' };
+
+const isSupportedEnvironment = () => typeof window !== 'undefined' && typeof window.localStorage !== 'undefined';
+
+const safeParse = (raw: string | null): SavedSignature[] => {
+  if (!raw) {
+    return [];
+  }
+
+  try {
+    const parsed = JSON.parse(raw);
+    if (!Array.isArray(parsed)) {
+      return [];
+    }
+
+    return parsed.filter((entry: any): entry is SavedSignature => {
+      if (!entry || typeof entry !== 'object') {
+        return false;
+      }
+      if (typeof entry.id !== 'string' || typeof entry.label !== 'string') {
+        return false;
+      }
+      if (typeof entry.type !== 'string') {
+        return false;
+      }
+
+      if (entry.type === 'text') {
+        return (
+          typeof entry.signerName === 'string' &&
+          typeof entry.fontFamily === 'string' &&
+          typeof entry.fontSize === 'number' &&
+          typeof entry.textColor === 'string'
+        );
+      }
+
+      return typeof entry.dataUrl === 'string';
+    });
+  } catch {
+    return [];
+  }
+};
+
+const readFromStorage = (): SavedSignature[] => {
+  if (!isSupportedEnvironment()) {
+    return [];
+  }
+
+  try {
+    return safeParse(window.localStorage.getItem(STORAGE_KEY));
+  } catch {
+    return [];
+  }
+};
+
+const writeToStorage = (entries: SavedSignature[]) => {
+  if (!isSupportedEnvironment()) {
+    return;
+  }
+
+  try {
+    window.localStorage.setItem(STORAGE_KEY, JSON.stringify(entries));
+  } catch {
+    // Swallow storage errors silently; we still keep state in memory.
+  }
+};
+
+const generateId = () => crypto.randomUUID();
+
+export const useSavedSignatures = () => {
+  const [savedSignatures, setSavedSignatures] = useState<SavedSignature[]>(() => readFromStorage());
+
+  useEffect(() => {
+    if (!isSupportedEnvironment()) {
+      return;
+    }
+
+    const syncFromStorage = () => {
+      setSavedSignatures(readFromStorage());
+    };
+
+    window.addEventListener('storage', syncFromStorage);
+    return () => window.removeEventListener('storage', syncFromStorage);
+  }, []);
+
+  useEffect(() => {
+    writeToStorage(savedSignatures);
+  }, [savedSignatures]);
+
+  const isAtCapacity = savedSignatures.length >= MAX_SAVED_SIGNATURES;
+
+  const addSignature = useCallback(
+    (payload: SavedSignaturePayload, label?: string): AddSignatureResult => {
+      if (
+        (payload.type === 'text' && !payload.signerName.trim()) ||
+        ((payload.type === 'canvas' || payload.type === 'image') && !payload.dataUrl)
+      ) {
+        return { success: false, reason: 'invalid' };
+      }
+
+      let createdSignature: SavedSignature | null = null;
+      setSavedSignatures(prev => {
+        if (prev.length >= MAX_SAVED_SIGNATURES) {
+          return prev;
+        }
+
+        const timestamp = Date.now();
+        const nextEntry: SavedSignature = {
+          ...payload,
+          id: generateId(),
+          label: (label || 'Signature').trim() || 'Signature',
+          createdAt: timestamp,
+          updatedAt: timestamp,
+        };
+        createdSignature = nextEntry;
+        return [nextEntry, ...prev];
+      });
+
+      return createdSignature
+        ? { success: true, signature: createdSignature }
+        : { success: false, reason: 'limit' };
+    },
+    []
+  );
+
+  const removeSignature = useCallback((id: string) => {
+    setSavedSignatures(prev => prev.filter(entry => entry.id !== id));
+  }, []);
+
+  const updateSignatureLabel = useCallback((id: string, nextLabel: string) => {
+    setSavedSignatures(prev =>
+      prev.map(entry =>
+        entry.id === id
+          ? { ...entry, label: nextLabel.trim() || entry.label || 'Signature', updatedAt: Date.now() }
+          : entry
+      )
+    );
+  }, []);
+
+  const replaceSignature = useCallback((id: string, payload: SavedSignaturePayload) => {
+    setSavedSignatures(prev =>
+      prev.map(entry =>
+        entry.id === id
+          ? {
+              ...entry,
+              ...payload,
+              updatedAt: Date.now(),
+            }
+          : entry
+      )
+    );
+  }, []);
+
+  const clearSignatures = useCallback(() => {
+    setSavedSignatures([]);
+  }, []);
+
+  const byTypeCounts = useMemo(() => {
+    return savedSignatures.reduce<Record<SavedSignatureType, number>>(
+      (acc, entry) => {
+        acc[entry.type] += 1;
+        return acc;
+      },
+      { canvas: 0, image: 0, text: 0 }
+    );
+  }, [savedSignatures]);
+
+  return {
+    savedSignatures,
+    isAtCapacity,
+    addSignature,
+    removeSignature,
+    updateSignatureLabel,
+    replaceSignature,
+    clearSignatures,
+    byTypeCounts,
+  };
+};
+
+export type UseSavedSignaturesReturn = ReturnType<typeof useSavedSignatures>;
diff --git a/frontend/src/core/hooks/tools/sign/useSignOperation.ts b/frontend/src/core/hooks/tools/sign/useSignOperation.ts
index 79bca1da8..9fc456fd4 100644
--- a/frontend/src/core/hooks/tools/sign/useSignOperation.ts
+++ b/frontend/src/core/hooks/tools/sign/useSignOperation.ts
@@ -23,7 +23,7 @@ export const buildSignFormData = (params: SignParameters, file: File): FormData
   }
 
   // Add signature type
-  formData.append('signatureType', params.signatureType || 'draw');
+  formData.append('signatureType', params.signatureType || 'canvas');
 
   // Add other parameters
   if (params.reason) {
@@ -56,4 +56,4 @@ export const useSignOperation = (): ToolOperationHook<SignParameters> => {
     ...signOperationConfig,
     getErrorMessage: createStandardErrorHandler(t('sign.error.failed', 'An error occurred while signing the PDF.'))
   });
-};
\ No newline at end of file
+};
diff --git a/frontend/src/core/hooks/tools/sign/useSignParameters.ts b/frontend/src/core/hooks/tools/sign/useSignParameters.ts
index f81097db6..c410afe3c 100644
--- a/frontend/src/core/hooks/tools/sign/useSignParameters.ts
+++ b/frontend/src/core/hooks/tools/sign/useSignParameters.ts
@@ -9,7 +9,7 @@ export interface SignaturePosition {
 }
 
 export interface SignParameters {
-  signatureType: 'image' | 'text' | 'draw' | 'canvas';
+  signatureType: 'image' | 'text' | 'canvas';
   signatureData?: string; // Base64 encoded image or text content
   signaturePosition?: SignaturePosition;
   reason?: string;
@@ -60,4 +60,4 @@ export const useSignParameters = () => {
     endpointName: 'add-signature',
     validateFn: validateSignParameters,
   });
-};
\ No newline at end of file
+};
diff --git a/frontend/src/core/hooks/useTooltipPosition.ts b/frontend/src/core/hooks/useTooltipPosition.ts
index 7b7d9a923..2510713c3 100644
--- a/frontend/src/core/hooks/useTooltipPosition.ts
+++ b/frontend/src/core/hooks/useTooltipPosition.ts
@@ -87,7 +87,7 @@ export function useTooltipPosition({
     if (sidebarTooltip) {
       // Require sidebar refs and state for proper positioning
       if (!sidebarRefs || !sidebarState) {
-        console.warn('⚠️ Sidebar tooltip requires sidebarRefs and sidebarState props');
+        console.warn('Sidebar tooltip requires sidebarRefs and sidebarState props');
         setPositionReady(false);
         return;
       }
@@ -97,7 +97,7 @@ export function useTooltipPosition({
 
       // Only show tooltip if we have the tool panel active
       if (!sidebarInfo.isToolPanelActive) {
-        console.log('🚫 Not showing tooltip - tool panel not active');
+        console.log('Not showing tooltip - tool panel not active');
         setPositionReady(false);
         return;
       }
diff --git a/frontend/src/core/services/apiClientSetup.ts b/frontend/src/core/services/apiClientSetup.ts
index f7de717a3..7bc356a7f 100644
--- a/frontend/src/core/services/apiClientSetup.ts
+++ b/frontend/src/core/services/apiClientSetup.ts
@@ -1,5 +1,14 @@
-import { AxiosInstance } from 'axios';
+import type { AxiosInstance } from 'axios';
+import { getBrowserId } from '@app/utils/browserIdentifier';
 
-export function setupApiInterceptors(_client: AxiosInstance): void {
-  // Core version: no interceptors to add
+export function setupApiInterceptors(client: AxiosInstance): void {
+  // Add browser ID header for WAU tracking
+  client.interceptors.request.use(
+    (config) => {
+      const browserId = getBrowserId();
+      config.headers['X-Browser-Id'] = browserId;
+      return config;
+    },
+    (error) => Promise.reject(error)
+  );
 }
diff --git a/frontend/src/core/services/supabaseClient.ts b/frontend/src/core/services/supabaseClient.ts
new file mode 100644
index 000000000..c0ace3002
--- /dev/null
+++ b/frontend/src/core/services/supabaseClient.ts
@@ -0,0 +1,20 @@
+import { createClient, SupabaseClient } from '@supabase/supabase-js';
+
+const supabaseUrl = import.meta.env.VITE_SUPABASE_URL;
+const supabaseAnonKey = import.meta.env.VITE_SUPABASE_PUBLISHABLE_DEFAULT_KEY;
+
+// Check if Supabase is configured
+export const isSupabaseConfigured = !!(supabaseUrl && supabaseAnonKey);
+
+// Create client only if configured, otherwise export null
+export const supabase: SupabaseClient | null = isSupabaseConfigured
+  ? createClient(supabaseUrl, supabaseAnonKey)
+  : null;
+
+// Log warning if not configured (for self-hosted installations)
+if (!isSupabaseConfigured) {
+  console.warn(
+    'Supabase is not configured. Checkout and billing features will be disabled. ' +
+    'Static plan information will be displayed instead.'
+  );
+}
diff --git a/frontend/src/core/services/updateService.ts b/frontend/src/core/services/updateService.ts
new file mode 100644
index 000000000..1cba4838f
--- /dev/null
+++ b/frontend/src/core/services/updateService.ts
@@ -0,0 +1,186 @@
+export interface UpdateSummary {
+  latest_version: string;
+  latest_stable_version?: string;
+  max_priority: 'urgent' | 'normal' | 'minor' | 'low';
+  recommended_action?: string;
+  any_breaking: boolean;
+  migration_guides?: Array<{
+    version: string;
+    notes: string;
+    url: string;
+  }>;
+}
+
+export interface VersionUpdate {
+  version: string;
+  priority: 'urgent' | 'normal' | 'minor' | 'low';
+  announcement: {
+    title: string;
+    message: string;
+  };
+  compatibility: {
+    breaking_changes: boolean;
+    breaking_description?: string;
+    migration_guide_url?: string;
+  };
+}
+
+export interface FullUpdateInfo {
+  latest_version: string;
+  latest_stable_version?: string;
+  new_versions: VersionUpdate[];
+}
+
+export interface MachineInfo {
+  machineType: string;
+  activeSecurity: boolean;
+  licenseType: string;
+}
+
+export class UpdateService {
+  private readonly baseUrl = 'https://supabase.stirling.com/functions/v1/updates';
+
+  /**
+   * Compare two version strings
+   * @returns 1 if v1 > v2, -1 if v1 < v2, 0 if equal
+   */
+  compareVersions(version1: string, version2: string): number {
+    const v1 = version1.split('.');
+    const v2 = version2.split('.');
+
+    for (let i = 0; i < v1.length || i < v2.length; i++) {
+      const n1 = parseInt(v1[i]) || 0;
+      const n2 = parseInt(v2[i]) || 0;
+
+      if (n1 > n2) {
+        return 1;
+      } else if (n1 < n2) {
+        return -1;
+      }
+    }
+
+    return 0;
+  }
+
+  /**
+   * Get download URL based on machine type and security settings
+   */
+  getDownloadUrl(machineInfo: MachineInfo): string | null {
+    // Only show download for non-Docker installations
+    if (machineInfo.machineType === 'Docker' || machineInfo.machineType === 'Kubernetes') {
+      return null;
+    }
+
+    const baseUrl = 'https://files.stirlingpdf.com/';
+
+    // Determine file based on machine type and security
+    if (machineInfo.machineType === 'Server-jar') {
+      return baseUrl + (machineInfo.activeSecurity ? 'Stirling-PDF-with-login.jar' : 'Stirling-PDF.jar');
+    }
+
+    // Client installations
+    if (machineInfo.machineType.startsWith('Client-')) {
+      const os = machineInfo.machineType.replace('Client-', ''); // win, mac, unix
+      const type = machineInfo.activeSecurity ? '-server-security' : '-server';
+
+      if (os === 'unix') {
+        return baseUrl + os + type + '.jar';
+      } else if (os === 'win') {
+        return baseUrl + os + '-installer.exe';
+      } else if (os === 'mac') {
+        return baseUrl + os + '-installer.dmg';
+      }
+    }
+
+    return null;
+  }
+
+  /**
+   * Fetch update summary from API
+   */
+  async getUpdateSummary(currentVersion: string, machineInfo: MachineInfo): Promise<UpdateSummary | null> {
+    // Map Java License enum to API types
+    let type = 'normal';
+    if (machineInfo.licenseType === 'PRO') {
+      type = 'pro';
+    } else if (machineInfo.licenseType === 'ENTERPRISE') {
+      type = 'enterprise';
+    }
+
+    const url = `${this.baseUrl}?from=${currentVersion}&type=${type}&login=${machineInfo.activeSecurity}&summary=true`;
+    console.log('Fetching update summary from:', url);
+
+    try {
+      const response = await fetch(url);
+      console.log('Response status:', response.status);
+
+      if (response.status === 200) {
+        const data = await response.json();
+        return data as UpdateSummary;
+      } else {
+        console.error('Failed to fetch update summary from Supabase:', response.status);
+        return null;
+      }
+    } catch (error) {
+      console.error('Failed to fetch update summary from Supabase:', error);
+      return null;
+    }
+  }
+
+  /**
+   * Fetch full update information with detailed version info
+   */
+  async getFullUpdateInfo(currentVersion: string, machineInfo: MachineInfo): Promise<FullUpdateInfo | null> {
+    // Map Java License enum to API types
+    let type = 'normal';
+    if (machineInfo.licenseType === 'PRO') {
+      type = 'pro';
+    } else if (machineInfo.licenseType === 'ENTERPRISE') {
+      type = 'enterprise';
+    }
+
+    const url = `${this.baseUrl}?from=${currentVersion}&type=${type}&login=${machineInfo.activeSecurity}&summary=false`;
+    console.log('Fetching full update info from:', url);
+
+    try {
+      const response = await fetch(url);
+      console.log('Full update response status:', response.status);
+
+      if (response.status === 200) {
+        const data = await response.json();
+        return data as FullUpdateInfo;
+      } else {
+        console.error('Failed to fetch full update info from Supabase:', response.status);
+        return null;
+      }
+    } catch (error) {
+      console.error('Failed to fetch full update info from Supabase:', error);
+      return null;
+    }
+  }
+
+  /**
+   * Get current version from GitHub build.gradle as fallback
+   */
+  async getCurrentVersionFromGitHub(): Promise<string> {
+    const url = 'https://raw.githubusercontent.com/Stirling-Tools/Stirling-PDF/master/build.gradle';
+
+    try {
+      const response = await fetch(url);
+      if (response.status === 200) {
+        const text = await response.text();
+        const versionRegex = /version\s*=\s*['"](\d+\.\d+\.\d+)['"]/;
+        const match = versionRegex.exec(text);
+        if (match) {
+          return match[1];
+        }
+      }
+      throw new Error('Version number not found');
+    } catch (error) {
+      console.error('Failed to fetch latest version from build.gradle:', error);
+      return '';
+    }
+  }
+}
+
+export const updateService = new UpdateService();
diff --git a/frontend/src/core/styles/zIndex.ts b/frontend/src/core/styles/zIndex.ts
index aeb69e9b5..1057bf2f2 100644
--- a/frontend/src/core/styles/zIndex.ts
+++ b/frontend/src/core/styles/zIndex.ts
@@ -15,7 +15,7 @@ export const Z_INDEX_HOVER_ACTION_MENU = 100;
 export const Z_INDEX_SELECTION_BOX = 1000;
 export const Z_INDEX_DROP_INDICATOR = 1001;
 export const Z_INDEX_DRAG_BADGE = 1001;
-// Modal that appears on top of config modal (e.g., restart confirmation)
+// Modal that appears on top of config modal (e.g., restart confirmation, update modal)
 export const Z_INDEX_OVER_CONFIG_MODAL = 2000;
 
 // Toast notifications and error displays - Always on top (higher than rainbow theme at 10000)
diff --git a/frontend/src/core/tools/Sign.tsx b/frontend/src/core/tools/Sign.tsx
index d8999a920..480d4c3a8 100644
--- a/frontend/src/core/tools/Sign.tsx
+++ b/frontend/src/core/tools/Sign.tsx
@@ -115,6 +115,32 @@ const Sign = (props: BaseToolProps) => {
         // Deactivate signature placement mode after everything completes
         handleDeactivateSignature();
 
+        const hasSignatureReady = (() => {
+          const params = base.params.parameters;
+          switch (params.signatureType) {
+            case 'canvas':
+            case 'image':
+              return Boolean(params.signatureData);
+            case 'text':
+              return Boolean(params.signerName && params.signerName.trim() !== '');
+            default:
+              return false;
+          }
+        })();
+
+        if (hasSignatureReady) {
+          if (typeof window !== 'undefined') {
+            // TODO: Ideally, we should trigger handleActivateSignaturePlacement when the viewer is ready.
+            // However, due to current architectural constraints, we use a 150ms delay to allow the viewer to reload.
+            // This value was empirically determined to be sufficient for most environments, but should be revisited.
+            window.setTimeout(() => {
+              handleActivateSignaturePlacement();
+            }, 150);
+          } else {
+            handleActivateSignaturePlacement();
+          }
+        }
+
         // File has been consumed - viewer should reload automatically via key prop
       } else {
         console.error('Signature flattening failed');
@@ -122,7 +148,7 @@ const Sign = (props: BaseToolProps) => {
     } catch (error) {
       console.error('Error saving signed document:', error);
     }
-  }, [exportActions, base.selectedFiles, selectors, consumeFiles, signatureApiRef, getImageData, setWorkbench, activateDrawMode, setSignaturesApplied, getScrollState, handleDeactivateSignature, setHasUnsavedChanges, unregisterUnsavedChangesChecker, activeFileIndex, setActiveFileIndex]);
+  }, [exportActions, base.selectedFiles, base.params.parameters, selectors, consumeFiles, signatureApiRef, getImageData, setWorkbench, activateDrawMode, setSignaturesApplied, getScrollState, handleDeactivateSignature, handleActivateSignaturePlacement, setHasUnsavedChanges, unregisterUnsavedChangesChecker, activeFileIndex, setActiveFileIndex]);
 
   const getSteps = () => {
     const steps = [];
@@ -179,4 +205,4 @@ Sign.getDefaultParameters = () => ({
   signerName: '',
 });
 
-export default Sign as ToolComponent;
\ No newline at end of file
+export default Sign as ToolComponent;
diff --git a/frontend/src/core/utils/browserIdentifier.ts b/frontend/src/core/utils/browserIdentifier.ts
new file mode 100644
index 000000000..b41914a5e
--- /dev/null
+++ b/frontend/src/core/utils/browserIdentifier.ts
@@ -0,0 +1,46 @@
+/**
+ * Browser identifier utility for anonymous usage tracking
+ * Generates and persists a unique UUID in localStorage for WAU tracking
+ */
+
+const BROWSER_ID_KEY = 'stirling_browser_id';
+
+/**
+ * Gets or creates a unique browser identifier
+ * Used for Weekly Active Users (WAU) tracking in no-login mode
+ */
+export function getBrowserId(): string {
+  try {
+    // Try to get existing ID from localStorage
+    let browserId = localStorage.getItem(BROWSER_ID_KEY);
+
+    if (!browserId) {
+      // Generate new UUID v4
+      browserId = generateUUID();
+      localStorage.setItem(BROWSER_ID_KEY, browserId);
+    }
+
+    return browserId;
+  } catch (error) {
+    // Fallback to session-based ID if localStorage is unavailable
+    console.warn('localStorage unavailable, using session-based ID', error);
+    return `session_${generateUUID()}`;
+  }
+}
+
+/**
+ * Generates a UUID v4
+ */
+function generateUUID(): string {
+  // Use crypto.randomUUID if available (modern browsers)
+  if (typeof crypto !== 'undefined' && crypto.randomUUID) {
+    return crypto.randomUUID();
+  }
+
+  // Fallback to manual UUID generation
+  return 'xxxxxxxx-xxxx-4xxx-yxxx-xxxxxxxxxxxx'.replace(/[xy]/g, (c) => {
+    const r = (Math.random() * 16) | 0;
+    const v = c === 'x' ? r : (r & 0x3) | 0x8;
+    return v.toString(16);
+  });
+}
diff --git a/frontend/src/core/utils/signatureFlattening.ts b/frontend/src/core/utils/signatureFlattening.ts
index 25c187020..f4c2fbed9 100644
--- a/frontend/src/core/utils/signatureFlattening.ts
+++ b/frontend/src/core/utils/signatureFlattening.ts
@@ -1,4 +1,5 @@
 import { PDFDocument, rgb } from 'pdf-lib';
+import { PdfAnnotationSubtype } from '@embedpdf/models';
 import { generateThumbnailWithMetadata } from '@app/utils/thumbnailUtils';
 import { createProcessedFile, createChildStub } from '@app/contexts/file/fileActions';
 import { createStirlingFile, StirlingFile, FileId, StirlingFileStub } from '@app/types/fileContext';
@@ -228,7 +229,7 @@ export async function flattenSignatures(options: SignatureFlatteningOptions): Pr
                         size: 12,
                         color: rgb(0, 0, 0)
                       });
-                    } else if (annotation.type === 14 || annotation.type === 15) {
+                    } else if (annotation.type === PdfAnnotationSubtype.INK || annotation.type === PdfAnnotationSubtype.LINE) {
                       // Handle ink annotations (drawn signatures)
                       page.drawRectangle({
                         x: pdfX,
diff --git a/frontend/src/core/utils/signaturePreview.ts b/frontend/src/core/utils/signaturePreview.ts
new file mode 100644
index 000000000..739edfb43
--- /dev/null
+++ b/frontend/src/core/utils/signaturePreview.ts
@@ -0,0 +1,84 @@
+import { SignParameters } from '@app/hooks/tools/sign/useSignParameters';
+import { HORIZONTAL_PADDING_RATIO, VERTICAL_PADDING_RATIO } from '@app/constants/signConstants';
+
+export interface SignaturePreview {
+  dataUrl: string;
+  width: number;
+  height: number;
+}
+
+const loadImage = (src: string): Promise<HTMLImageElement> =>
+  new Promise((resolve, reject) => {
+    const img = new Image();
+    img.onload = () => resolve(img);
+    img.onerror = reject;
+    img.src = src;
+  });
+
+export const buildSignaturePreview = async (config: SignParameters | null): Promise<SignaturePreview | null> => {
+  if (typeof window === 'undefined' || typeof document === 'undefined') {
+    return null;
+  }
+
+  if (!config) {
+    return null;
+  }
+
+  if (config.signatureType === 'text') {
+    const text = config.signerName?.trim();
+    if (!text) {
+      return null;
+    }
+
+    const fontSize = config.fontSize ?? 16;
+    const fontFamily = config.fontFamily ?? 'Helvetica';
+    const textColor = config.textColor ?? '#000000';
+
+    const paddingX = Math.round(fontSize * HORIZONTAL_PADDING_RATIO);
+    const paddingY = Math.round(fontSize * VERTICAL_PADDING_RATIO);
+
+    const measureCanvas = document.createElement('canvas');
+    const measureCtx = measureCanvas.getContext('2d');
+
+    if (!measureCtx) {
+      return null;
+    }
+
+    measureCtx.font = `${fontSize}px ${fontFamily}`;
+    const metrics = measureCtx.measureText(text);
+    const textWidth = Math.ceil(metrics.width);
+
+    const width = Math.max(1, textWidth + paddingX * 2);
+    const height = Math.max(1, Math.ceil(fontSize + paddingY * 2));
+
+    const canvas = document.createElement('canvas');
+    canvas.width = width;
+    canvas.height = height;
+
+    const ctx = canvas.getContext('2d');
+    if (!ctx) {
+      return null;
+    }
+
+    ctx.fillStyle = textColor;
+    ctx.font = `${fontSize}px ${fontFamily}`;
+    ctx.textBaseline = 'middle';
+    ctx.textAlign = 'left';
+    ctx.fillText(text, paddingX, height / 2);
+
+    const dataUrl = canvas.toDataURL('image/png');
+    return { dataUrl, width, height };
+  }
+
+  const dataUrl = config.signatureData;
+  if (!dataUrl) {
+    return null;
+  }
+
+  const image = await loadImage(dataUrl);
+  return {
+    dataUrl,
+    width: image.naturalWidth || image.width,
+    height: image.naturalHeight || image.height,
+  };
+};
diff --git a/frontend/src/desktop/components/AppProviders.tsx b/frontend/src/desktop/components/AppProviders.tsx
index f5363b5e7..f6fc1ea1b 100644
--- a/frontend/src/desktop/components/AppProviders.tsx
+++ b/frontend/src/desktop/components/AppProviders.tsx
@@ -1,15 +1,66 @@
-import { ReactNode } from "react";
+import { ReactNode, useEffect, useState } from "react";
 import { AppProviders as ProprietaryAppProviders } from "@proprietary/components/AppProviders";
 import { DesktopConfigSync } from '@app/components/DesktopConfigSync';
 import { DesktopBannerInitializer } from '@app/components/DesktopBannerInitializer';
+import { SetupWizard } from '@app/components/SetupWizard';
+import { useFirstLaunchCheck } from '@app/hooks/useFirstLaunchCheck';
+import { useBackendInitializer } from '@app/hooks/useBackendInitializer';
 import { DESKTOP_DEFAULT_APP_CONFIG } from '@app/config/defaultAppConfig';
+import { connectionModeService } from '@desktop/services/connectionModeService';
+import { tauriBackendService } from '@app/services/tauriBackendService';
 
 /**
  * Desktop application providers
  * Wraps proprietary providers and adds desktop-specific configuration
  * - Enables retry logic for app config (needed for Tauri mode when backend is starting)
+ * - Shows setup wizard on first launch
  */
 export function AppProviders({ children }: { children: ReactNode }) {
+  const { isFirstLaunch, setupComplete } = useFirstLaunchCheck();
+  const [connectionMode, setConnectionMode] = useState<'offline' | 'server' | null>(null);
+
+  // Load connection mode on mount
+  useEffect(() => {
+    void connectionModeService.getCurrentMode().then(setConnectionMode);
+  }, []);
+
+  // Initialize backend health monitoring for server mode
+  useEffect(() => {
+    if (setupComplete && !isFirstLaunch && connectionMode === 'server') {
+      console.log('[AppProviders] Initializing external backend monitoring for server mode');
+      void tauriBackendService.initializeExternalBackend();
+    }
+  }, [setupComplete, isFirstLaunch, connectionMode]);
+
+  // Only start bundled backend if in offline mode and setup is complete
+  const shouldStartBackend = setupComplete && !isFirstLaunch && connectionMode === 'offline';
+  useBackendInitializer(shouldStartBackend);
+
+  // Show setup wizard on first launch
+  if (isFirstLaunch && !setupComplete) {
+    return (
+      <ProprietaryAppProviders
+        appConfigRetryOptions={{
+          maxRetries: 5,
+          initialDelay: 1000,
+        }}
+        appConfigProviderProps={{
+          initialConfig: DESKTOP_DEFAULT_APP_CONFIG,
+          bootstrapMode: 'non-blocking',
+          autoFetch: false,
+        }}
+      >
+        <SetupWizard
+          onComplete={() => {
+            // Reload the page to reinitialize with new connection config
+            window.location.reload();
+          }}
+        />
+      </ProprietaryAppProviders>
+    );
+  }
+
+  // Normal app flow
   return (
     <ProprietaryAppProviders
       appConfigRetryOptions={{
diff --git a/frontend/src/desktop/components/ConnectionSettings.tsx b/frontend/src/desktop/components/ConnectionSettings.tsx
new file mode 100644
index 000000000..da7e2cb61
--- /dev/null
+++ b/frontend/src/desktop/components/ConnectionSettings.tsx
@@ -0,0 +1,287 @@
+import React, { useState, useEffect } from 'react';
+import { Stack, Card, Badge, Button, Text, Group, Modal, TextInput, Radio } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import {
+  connectionModeService,
+  ConnectionConfig,
+  ServerConfig,
+} from '@app/services/connectionModeService';
+import { authService, UserInfo } from '@app/services/authService';
+import { LoginForm } from '@app/components/SetupWizard/LoginForm';
+import { STIRLING_SAAS_URL } from '@app/constants/connection';
+import { Z_INDEX_OVER_CONFIG_MODAL } from '@app/styles/zIndex';
+
+export const ConnectionSettings: React.FC = () => {
+  const { t } = useTranslation();
+  const [config, setConfig] = useState<ConnectionConfig | null>(null);
+  const [userInfo, setUserInfo] = useState<UserInfo | null>(null);
+  const [loading, setLoading] = useState(false);
+  const [showServerModal, setShowServerModal] = useState(false);
+  const [showLoginModal, setShowLoginModal] = useState(false);
+  const [newServerConfig, setNewServerConfig] = useState<ServerConfig | null>(null);
+
+  // Load current config on mount
+  useEffect(() => {
+    const loadConfig = async () => {
+      const currentConfig = await connectionModeService.getCurrentConfig();
+      setConfig(currentConfig);
+
+      if (currentConfig.mode === 'server') {
+        const user = await authService.getUserInfo();
+        setUserInfo(user);
+      }
+    };
+
+    loadConfig();
+  }, []);
+
+  const handleSwitchToOffline = async () => {
+    try {
+      setLoading(true);
+      await connectionModeService.switchToOffline();
+
+      // Reload config
+      const newConfig = await connectionModeService.getCurrentConfig();
+      setConfig(newConfig);
+      setUserInfo(null);
+
+      // Reload the page to start the local backend
+      window.location.reload();
+    } catch (error) {
+      console.error('Failed to switch to offline:', error);
+    } finally {
+      setLoading(false);
+    }
+  };
+
+  const handleSwitchToServer = () => {
+    setShowServerModal(true);
+  };
+
+  const handleServerConfigSubmit = (serverConfig: ServerConfig) => {
+    setNewServerConfig(serverConfig);
+    setShowServerModal(false);
+    setShowLoginModal(true);
+  };
+
+  const handleLogin = async (username: string, password: string) => {
+    if (!newServerConfig) return;
+
+    try {
+      setLoading(true);
+
+      // Login
+      await authService.login(newServerConfig.url, username, password);
+
+      // Switch to server mode
+      await connectionModeService.switchToServer(newServerConfig);
+
+      // Reload config and user info
+      const newConfig = await connectionModeService.getCurrentConfig();
+      setConfig(newConfig);
+      const user = await authService.getUserInfo();
+      setUserInfo(user);
+
+      setShowLoginModal(false);
+      setNewServerConfig(null);
+
+      // Reload the page to stop local backend and initialize external backend monitoring
+      window.location.reload();
+    } catch (error) {
+      console.error('Login failed:', error);
+      throw error; // Let LoginForm handle the error
+    } finally {
+      setLoading(false);
+    }
+  };
+
+  const handleLogout = async () => {
+    try {
+      setLoading(true);
+      await authService.logout();
+
+      // Switch to offline mode
+      await connectionModeService.switchToOffline();
+
+      // Reload config
+      const newConfig = await connectionModeService.getCurrentConfig();
+      setConfig(newConfig);
+      setUserInfo(null);
+
+      // Reload the page to clear all state and reconnect to local backend
+      window.location.reload();
+    } catch (error) {
+      console.error('Logout failed:', error);
+    } finally {
+      setLoading(false);
+    }
+  };
+
+  if (!config) {
+    return <Text>{t('common.loading', 'Loading...')}</Text>;
+  }
+
+  return (
+    <>
+      <Card shadow="sm" padding="lg" radius="md" withBorder>
+        <Stack gap="md">
+          <Group justify="space-between">
+            <Text fw={600}>{t('settings.connection.title', 'Connection Mode')}</Text>
+            <Badge color={config.mode === 'offline' ? 'blue' : 'green'} variant="light">
+              {config.mode === 'offline'
+                ? t('settings.connection.mode.offline', 'Offline')
+                : t('settings.connection.mode.server', 'Server')}
+            </Badge>
+          </Group>
+
+          {config.mode === 'server' && config.server_config && (
+            <>
+              <div>
+                <Text size="sm" fw={500}>
+                  {t('settings.connection.server', 'Server')}
+                </Text>
+                <Text size="sm" c="dimmed">
+                  {config.server_config.url}
+                </Text>
+              </div>
+
+              {userInfo && (
+                <div>
+                  <Text size="sm" fw={500}>
+                    {t('settings.connection.user', 'Logged in as')}
+                  </Text>
+                  <Text size="sm" c="dimmed">
+                    {userInfo.username}
+                    {userInfo.email && ` (${userInfo.email})`}
+                  </Text>
+                </div>
+              )}
+            </>
+          )}
+
+          <Group mt="md">
+            {config.mode === 'offline' ? (
+              <Button onClick={handleSwitchToServer} disabled={loading}>
+                {t('settings.connection.switchToServer', 'Connect to Server')}
+              </Button>
+            ) : (
+              <>
+                <Button onClick={handleSwitchToOffline} variant="default" disabled={loading}>
+                  {t('settings.connection.switchToOffline', 'Switch to Offline')}
+                </Button>
+                <Button onClick={handleLogout} color="red" variant="light" disabled={loading}>
+                  {t('settings.connection.logout', 'Logout')}
+                </Button>
+              </>
+            )}
+          </Group>
+        </Stack>
+      </Card>
+
+      {/* Server selection modal */}
+      <Modal
+        opened={showServerModal}
+        onClose={() => setShowServerModal(false)}
+        title={t('settings.connection.selectServer', 'Select Server')}
+        zIndex={Z_INDEX_OVER_CONFIG_MODAL}
+      >
+        <ServerSelectionInSettings onSubmit={handleServerConfigSubmit} />
+      </Modal>
+
+      {/* Login modal */}
+      <Modal
+        opened={showLoginModal}
+        onClose={() => {
+          setShowLoginModal(false);
+          setNewServerConfig(null);
+        }}
+        title={t('settings.connection.login', 'Login')}
+        zIndex={Z_INDEX_OVER_CONFIG_MODAL}
+      >
+        {newServerConfig && (
+          <LoginForm
+            serverUrl={newServerConfig.url}
+            onLogin={handleLogin}
+            loading={loading}
+          />
+        )}
+      </Modal>
+    </>
+  );
+};
+
+// Mini server selection component for settings
+const ServerSelectionInSettings: React.FC<{ onSubmit: (config: ServerConfig) => void }> = ({
+  onSubmit,
+}) => {
+  const { t } = useTranslation();
+  const [serverType, setServerType] = useState<'saas' | 'selfhosted'>('saas');
+  const [customUrl, setCustomUrl] = useState('');
+  const [testing, setTesting] = useState(false);
+  const [error, setError] = useState<string | null>(null);
+
+  const handleSubmit = async () => {
+    const url = serverType === 'saas' ? STIRLING_SAAS_URL : customUrl.trim();
+
+    if (!url) {
+      setError(t('setup.server.error.emptyUrl', 'Please enter a server URL'));
+      return;
+    }
+
+    setTesting(true);
+    setError(null);
+
+    try {
+      const isReachable = await connectionModeService.testConnection(url);
+
+      if (!isReachable) {
+        setError(t('setup.server.error.unreachable', 'Could not connect to server'));
+        setTesting(false);
+        return;
+      }
+
+      onSubmit({
+        url,
+        server_type: serverType,
+      });
+    } catch (err) {
+      setError(err instanceof Error ? err.message : t('setup.server.error.testFailed', 'Connection test failed'));
+      setTesting(false);
+    }
+  };
+
+  return (
+    <Stack gap="md">
+      <Radio.Group value={serverType} onChange={(value) => setServerType(value as 'saas' | 'selfhosted')}>
+        <Stack gap="xs">
+          <Radio value="saas" label={t('setup.server.type.saas', 'Stirling PDF SaaS')} />
+          <Radio value="selfhosted" label={t('setup.server.type.selfhosted', 'Self-hosted server')} />
+        </Stack>
+      </Radio.Group>
+
+      {serverType === 'selfhosted' && (
+        <TextInput
+          label={t('setup.server.url.label', 'Server URL')}
+          placeholder="https://your-server.com"
+          value={customUrl}
+          onChange={(e) => {
+            setCustomUrl(e.target.value);
+            setError(null);
+          }}
+          disabled={testing}
+          error={error}
+        />
+      )}
+
+      {error && !customUrl && (
+        <Text c="red" size="sm">
+          {error}
+        </Text>
+      )}
+
+      <Button onClick={handleSubmit} loading={testing} fullWidth>
+        {testing ? t('setup.server.testing', 'Testing...') : t('common.continue', 'Continue')}
+      </Button>
+    </Stack>
+  );
+};
diff --git a/frontend/src/desktop/components/SetupWizard/LoginForm.tsx b/frontend/src/desktop/components/SetupWizard/LoginForm.tsx
new file mode 100644
index 000000000..be9951995
--- /dev/null
+++ b/frontend/src/desktop/components/SetupWizard/LoginForm.tsx
@@ -0,0 +1,85 @@
+import React, { useState } from 'react';
+import { Stack, TextInput, PasswordInput, Button, Text } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+
+interface LoginFormProps {
+  serverUrl: string;
+  onLogin: (username: string, password: string) => Promise<void>;
+  loading: boolean;
+}
+
+export const LoginForm: React.FC<LoginFormProps> = ({ serverUrl, onLogin, loading }) => {
+  const { t } = useTranslation();
+  const [username, setUsername] = useState('');
+  const [password, setPassword] = useState('');
+  const [validationError, setValidationError] = useState<string | null>(null);
+
+  const handleSubmit = async (e: React.FormEvent) => {
+    e.preventDefault();
+
+    // Validation
+    if (!username.trim()) {
+      setValidationError(t('setup.login.error.emptyUsername', 'Please enter your username'));
+      return;
+    }
+
+    if (!password) {
+      setValidationError(t('setup.login.error.emptyPassword', 'Please enter your password'));
+      return;
+    }
+
+    setValidationError(null);
+    await onLogin(username.trim(), password);
+  };
+
+  return (
+    <form onSubmit={handleSubmit}>
+      <Stack gap="md">
+        <Text size="sm" c="dimmed">
+          {t('setup.login.connectingTo', 'Connecting to:')} <strong>{serverUrl}</strong>
+        </Text>
+
+        <TextInput
+          label={t('setup.login.username.label', 'Username')}
+          placeholder={t('setup.login.username.placeholder', 'Enter your username')}
+          value={username}
+          onChange={(e) => {
+            setUsername(e.target.value);
+            setValidationError(null);
+          }}
+          disabled={loading}
+          required
+        />
+
+        <PasswordInput
+          label={t('setup.login.password.label', 'Password')}
+          placeholder={t('setup.login.password.placeholder', 'Enter your password')}
+          value={password}
+          onChange={(e) => {
+            setPassword(e.target.value);
+            setValidationError(null);
+          }}
+          disabled={loading}
+          required
+        />
+
+        {validationError && (
+          <Text c="red" size="sm">
+            {validationError}
+          </Text>
+        )}
+
+        <Button
+          type="submit"
+          loading={loading}
+          disabled={loading}
+          mt="md"
+          fullWidth
+          color="#AF3434"
+        >
+          {t('setup.login.submit', 'Login')}
+        </Button>
+      </Stack>
+    </form>
+  );
+};
diff --git a/frontend/src/desktop/components/SetupWizard/ModeSelection.tsx b/frontend/src/desktop/components/SetupWizard/ModeSelection.tsx
new file mode 100644
index 000000000..0512081d5
--- /dev/null
+++ b/frontend/src/desktop/components/SetupWizard/ModeSelection.tsx
@@ -0,0 +1,66 @@
+import React from 'react';
+import { Stack, Button, Text } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import CloudIcon from '@mui/icons-material/Cloud';
+import ComputerIcon from '@mui/icons-material/Computer';
+
+interface ModeSelectionProps {
+  onSelect: (mode: 'offline' | 'server') => void;
+  loading: boolean;
+}
+
+export const ModeSelection: React.FC<ModeSelectionProps> = ({ onSelect, loading }) => {
+  const { t } = useTranslation();
+
+  return (
+    <Stack gap="md">
+      <Button
+        size="xl"
+        variant="default"
+        onClick={() => onSelect('offline')}
+        disabled={loading}
+        leftSection={<ComputerIcon />}
+        styles={{
+          root: {
+            height: 'auto',
+            padding: '1.25rem',
+          },
+          inner: {
+            justifyContent: 'flex-start',
+          },
+        }}
+      >
+        <div style={{ textAlign: 'left', flex: 1 }}>
+          <Text fw={600} size="md">{t('setup.mode.offline.title', 'Use Offline')}</Text>
+          <Text size="sm" c="dimmed" fw={400}>
+            {t('setup.mode.offline.description', 'Run locally without an internet connection')}
+          </Text>
+        </div>
+      </Button>
+
+      <Button
+        size="xl"
+        variant="default"
+        onClick={() => onSelect('server')}
+        disabled={loading}
+        leftSection={<CloudIcon />}
+        styles={{
+          root: {
+            height: 'auto',
+            padding: '1.25rem',
+          },
+          inner: {
+            justifyContent: 'flex-start',
+          },
+        }}
+      >
+        <div style={{ textAlign: 'left', flex: 1 }}>
+          <Text fw={600} size="md">{t('setup.mode.server.title', 'Connect to Server')}</Text>
+          <Text size="sm" c="dimmed" fw={400}>
+            {t('setup.mode.server.description', 'Connect to a remote Stirling PDF server')}
+          </Text>
+        </div>
+      </Button>
+    </Stack>
+  );
+};
diff --git a/frontend/src/desktop/components/SetupWizard/ServerSelection.tsx b/frontend/src/desktop/components/SetupWizard/ServerSelection.tsx
new file mode 100644
index 000000000..7d0f8de1e
--- /dev/null
+++ b/frontend/src/desktop/components/SetupWizard/ServerSelection.tsx
@@ -0,0 +1,92 @@
+import React, { useState } from 'react';
+import { Stack, Button, TextInput } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import { ServerConfig } from '@app/services/connectionModeService';
+import { connectionModeService } from '@app/services/connectionModeService';
+
+interface ServerSelectionProps {
+  onSelect: (config: ServerConfig) => void;
+  loading: boolean;
+}
+
+export const ServerSelection: React.FC<ServerSelectionProps> = ({ onSelect, loading }) => {
+  const { t } = useTranslation();
+  const [customUrl, setCustomUrl] = useState('');
+  const [testing, setTesting] = useState(false);
+  const [testError, setTestError] = useState<string | null>(null);
+
+  const handleSubmit = async (e: React.FormEvent) => {
+    e.preventDefault();
+
+    const url = customUrl.trim();
+
+    if (!url) {
+      setTestError(t('setup.server.error.emptyUrl', 'Please enter a server URL'));
+      return;
+    }
+
+    // Test connection before proceeding
+    setTesting(true);
+    setTestError(null);
+
+    try {
+      const isReachable = await connectionModeService.testConnection(url);
+
+      if (!isReachable) {
+        setTestError(t('setup.server.error.unreachable', 'Could not connect to server'));
+        setTesting(false);
+        return;
+      }
+
+      // Connection successful
+      onSelect({
+        url,
+        server_type: 'selfhosted',
+      });
+    } catch (error) {
+      console.error('Connection test failed:', error);
+      setTestError(
+        error instanceof Error
+          ? error.message
+          : t('setup.server.error.testFailed', 'Connection test failed')
+      );
+    } finally {
+      setTesting(false);
+    }
+  };
+
+  return (
+    <form onSubmit={handleSubmit}>
+      <Stack gap="md">
+        <TextInput
+          label={t('setup.server.url.label', 'Server URL')}
+          placeholder="https://your-server.com"
+          value={customUrl}
+          onChange={(e) => {
+            setCustomUrl(e.target.value);
+            setTestError(null);
+          }}
+          disabled={loading || testing}
+          error={testError}
+          description={t(
+            'setup.server.url.description',
+            'Enter the full URL of your self-hosted Stirling PDF server'
+          )}
+        />
+
+        <Button
+          type="submit"
+          loading={testing || loading}
+          disabled={loading}
+          mt="md"
+          fullWidth
+          color="#AF3434"
+        >
+          {testing
+            ? t('setup.server.testing', 'Testing connection...')
+            : t('common.continue', 'Continue')}
+        </Button>
+      </Stack>
+    </form>
+  );
+};
diff --git a/frontend/src/desktop/components/SetupWizard/SetupWizard.css b/frontend/src/desktop/components/SetupWizard/SetupWizard.css
new file mode 100644
index 000000000..3f89cf572
--- /dev/null
+++ b/frontend/src/desktop/components/SetupWizard/SetupWizard.css
@@ -0,0 +1,20 @@
+.setup-container {
+  position: relative;
+  min-height: 100vh;
+  display: flex;
+  flex-direction: column;
+  align-items: center;
+  justify-content: center;
+  background: linear-gradient(135deg, #f5f5f5 0%, #e8e8e8 100%);
+  padding: 2rem;
+}
+
+.setup-wrapper {
+  width: 100%;
+  max-width: 600px;
+}
+
+.setup-card {
+  background-color: white;
+  box-shadow: 0 20px 60px rgba(0, 0, 0, 0.12);
+}
diff --git a/frontend/src/desktop/components/SetupWizard/index.tsx b/frontend/src/desktop/components/SetupWizard/index.tsx
new file mode 100644
index 000000000..3b47245e0
--- /dev/null
+++ b/frontend/src/desktop/components/SetupWizard/index.tsx
@@ -0,0 +1,184 @@
+import React, { useState } from 'react';
+import { Container, Paper, Stack, Title, Text, Button, Image } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import { ModeSelection } from '@app/components/SetupWizard/ModeSelection';
+import { ServerSelection } from '@app/components/SetupWizard/ServerSelection';
+import { LoginForm } from '@app/components/SetupWizard/LoginForm';
+import { connectionModeService, ServerConfig } from '@app/services/connectionModeService';
+import { authService } from '@app/services/authService';
+import { tauriBackendService } from '@app/services/tauriBackendService';
+import { BASE_PATH } from '@app/constants/app';
+import '@app/components/SetupWizard/SetupWizard.css';
+
+enum SetupStep {
+  ModeSelection,
+  ServerSelection,
+  Login,
+}
+
+interface SetupWizardProps {
+  onComplete: () => void;
+}
+
+export const SetupWizard: React.FC<SetupWizardProps> = ({ onComplete }) => {
+  const { t } = useTranslation();
+  const [activeStep, setActiveStep] = useState<SetupStep>(SetupStep.ModeSelection);
+  const [_selectedMode, setSelectedMode] = useState<'offline' | 'server' | null>(null);
+  const [serverConfig, setServerConfig] = useState<ServerConfig | null>(null);
+  const [loading, setLoading] = useState(false);
+  const [error, setError] = useState<string | null>(null);
+
+  const handleModeSelection = (mode: 'offline' | 'server') => {
+    setSelectedMode(mode);
+    setError(null);
+
+    if (mode === 'offline') {
+      handleOfflineSetup();
+    } else {
+      setActiveStep(SetupStep.ServerSelection);
+    }
+  };
+
+  const handleOfflineSetup = async () => {
+    try {
+      setLoading(true);
+      setError(null);
+
+      await connectionModeService.switchToOffline();
+      await tauriBackendService.startBackend();
+      onComplete();
+    } catch (err) {
+      console.error('Failed to set up offline mode:', err);
+      setError(err instanceof Error ? err.message : 'Failed to set up offline mode');
+      setLoading(false);
+    }
+  };
+
+  const handleServerSelection = (config: ServerConfig) => {
+    setServerConfig(config);
+    setError(null);
+    setActiveStep(SetupStep.Login);
+  };
+
+  const handleLogin = async (username: string, password: string) => {
+    if (!serverConfig) {
+      setError('No server configured');
+      return;
+    }
+
+    try {
+      setLoading(true);
+      setError(null);
+
+      await authService.login(serverConfig.url, username, password);
+      await connectionModeService.switchToServer(serverConfig);
+      await tauriBackendService.initializeExternalBackend();
+      onComplete();
+    } catch (err) {
+      console.error('Login failed:', err);
+      setError(err instanceof Error ? err.message : 'Login failed');
+      setLoading(false);
+    }
+  };
+
+  const handleBack = () => {
+    setError(null);
+    if (activeStep === SetupStep.Login) {
+      setActiveStep(SetupStep.ServerSelection);
+    } else if (activeStep === SetupStep.ServerSelection) {
+      setActiveStep(SetupStep.ModeSelection);
+      setSelectedMode(null);
+      setServerConfig(null);
+    }
+  };
+
+  const getStepTitle = () => {
+    switch (activeStep) {
+      case SetupStep.ModeSelection:
+        return t('setup.welcome', 'Welcome to Stirling PDF');
+      case SetupStep.ServerSelection:
+        return t('setup.server.title', 'Connect to Server');
+      case SetupStep.Login:
+        return t('setup.login.title', 'Sign In');
+      default:
+        return '';
+    }
+  };
+
+  const getStepSubtitle = () => {
+    switch (activeStep) {
+      case SetupStep.ModeSelection:
+        return t('setup.description', 'Get started by choosing how you want to use Stirling PDF');
+      case SetupStep.ServerSelection:
+        return t('setup.server.subtitle', 'Enter your self-hosted server URL');
+      case SetupStep.Login:
+        return t('setup.login.subtitle', 'Enter your credentials to continue');
+      default:
+        return '';
+    }
+  };
+
+  return (
+    <div className="setup-container">
+      <Container size="sm" className="setup-wrapper">
+        <Paper shadow="xl" p="xl" radius="lg" className="setup-card">
+          <Stack gap="lg">
+            {/* Logo Header */}
+            <Stack gap="xs" align="center">
+              <Image
+                src={`${BASE_PATH}/branding/StirlingPDFLogoBlackText.svg`}
+                alt="Stirling PDF"
+                h={32}
+                fit="contain"
+              />
+              <Title order={1} ta="center" style={{ fontSize: '2rem', fontWeight: 800 }}>
+                {getStepTitle()}
+              </Title>
+              <Text size="sm" c="dimmed" ta="center">
+                {getStepSubtitle()}
+              </Text>
+            </Stack>
+
+            {/* Error Message */}
+            {error && (
+              <Paper p="md" bg="red.0" style={{ border: '1px solid var(--mantine-color-red-3)' }}>
+                <Text size="sm" c="red.7" ta="center">
+                  {error}
+                </Text>
+              </Paper>
+            )}
+
+            {/* Step Content */}
+            {activeStep === SetupStep.ModeSelection && (
+              <ModeSelection onSelect={handleModeSelection} loading={loading} />
+            )}
+
+            {activeStep === SetupStep.ServerSelection && (
+              <ServerSelection onSelect={handleServerSelection} loading={loading} />
+            )}
+
+            {activeStep === SetupStep.Login && (
+              <LoginForm
+                serverUrl={serverConfig?.url || ''}
+                onLogin={handleLogin}
+                loading={loading}
+              />
+            )}
+
+            {/* Back Button */}
+            {activeStep > SetupStep.ModeSelection && !loading && (
+              <Button
+                variant="subtle"
+                onClick={handleBack}
+                fullWidth
+                mt="md"
+              >
+                {t('common.back', 'Back')}
+              </Button>
+            )}
+          </Stack>
+        </Paper>
+      </Container>
+    </div>
+  );
+};
diff --git a/frontend/src/desktop/components/shared/config/configNavSections.tsx b/frontend/src/desktop/components/shared/config/configNavSections.tsx
new file mode 100644
index 000000000..3582ccb99
--- /dev/null
+++ b/frontend/src/desktop/components/shared/config/configNavSections.tsx
@@ -0,0 +1,30 @@
+import { createConfigNavSections as createProprietaryConfigNavSections } from '@proprietary/components/shared/config/configNavSections';
+import { ConfigNavSection } from '@core/components/shared/config/configNavSections';
+import { ConnectionSettings } from '@app/components/ConnectionSettings';
+
+/**
+ * Desktop extension of createConfigNavSections that adds connection settings
+ */
+export const createConfigNavSections = (
+  isAdmin: boolean = false,
+  runningEE: boolean = false,
+  loginEnabled: boolean = false
+): ConfigNavSection[] => {
+  // Get the proprietary sections (includes core Preferences + admin sections)
+  const sections = createProprietaryConfigNavSections(isAdmin, runningEE, loginEnabled);
+
+  // Add Connection section at the beginning (after Preferences)
+  sections.splice(1, 0, {
+    title: 'Connection',
+    items: [
+      {
+        key: 'connectionMode',
+        label: 'Connection Mode',
+        icon: 'cloud-rounded',
+        component: <ConnectionSettings />,
+      },
+    ],
+  });
+
+  return sections;
+};
diff --git a/frontend/src/desktop/components/shared/config/types.ts b/frontend/src/desktop/components/shared/config/types.ts
new file mode 100644
index 000000000..cdbf0558a
--- /dev/null
+++ b/frontend/src/desktop/components/shared/config/types.ts
@@ -0,0 +1,8 @@
+import { VALID_NAV_KEYS as CORE_NAV_KEYS } from '@core/components/shared/config/types';
+
+export const VALID_NAV_KEYS = [
+  ...CORE_NAV_KEYS,
+  'connectionMode',
+] as const;
+
+export type NavKey = typeof VALID_NAV_KEYS[number];
diff --git a/frontend/src/desktop/constants/connection.ts b/frontend/src/desktop/constants/connection.ts
new file mode 100644
index 000000000..b9ba31f77
--- /dev/null
+++ b/frontend/src/desktop/constants/connection.ts
@@ -0,0 +1,5 @@
+/**
+ * Connection-related constants for desktop app
+ */
+
+export const STIRLING_SAAS_URL = 'https://stirling.com/app';
diff --git a/frontend/src/desktop/hooks/useAppInitialization.ts b/frontend/src/desktop/hooks/useAppInitialization.ts
index 1ef8ef694..68b5fc219 100644
--- a/frontend/src/desktop/hooks/useAppInitialization.ts
+++ b/frontend/src/desktop/hooks/useAppInitialization.ts
@@ -1,19 +1,15 @@
-import { useEffect } from 'react';
-import { useBackendInitializer } from '@app/hooks/useBackendInitializer';
+import { useEffect, useState } from 'react';
 import { useOpenedFile } from '@app/hooks/useOpenedFile';
 import { fileOpenService } from '@app/services/fileOpenService';
 import { useFileManagement } from '@app/contexts/file/fileHooks';
 
 /**
  * App initialization hook
- * Desktop version: Handles Tauri-specific initialization
- * - Starts the backend on app startup
+ * Desktop version: Handles Tauri-specific file initialization
+ * Requires FileContext - must be used inside FileContextProvider
  * - Handles files opened with the app (adds directly to FileContext)
  */
 export function useAppInitialization(): void {
-  // Initialize backend on app startup
-  useBackendInitializer();
-
   // Get file management actions
   const { addFiles } = useFileManagement();
 
@@ -59,3 +55,11 @@ export function useAppInitialization(): void {
     loadOpenedFiles();
   }, [openedFilePaths, openedFileLoading, addFiles]);
 }
+
+export function useSetupCompletion(): (completed: boolean) => void {
+  const [, setSetupComplete] = useState(false);
+
+  return (completed: boolean) => {
+    setSetupComplete(completed);
+  };
+}
diff --git a/frontend/src/desktop/hooks/useBackendInitializer.ts b/frontend/src/desktop/hooks/useBackendInitializer.ts
index 259f4d875..e14c7ea53 100644
--- a/frontend/src/desktop/hooks/useBackendInitializer.ts
+++ b/frontend/src/desktop/hooks/useBackendInitializer.ts
@@ -5,12 +5,18 @@ import { tauriBackendService } from '@app/services/tauriBackendService';
 
 /**
  * Hook to initialize backend and monitor health
+ * @param enabled - Whether to initialize the backend (default: true)
  */
-export function useBackendInitializer() {
+export function useBackendInitializer(enabled = true) {
   const { status, checkHealth } = useBackendHealth();
   const { backendUrl } = useEndpointConfig();
 
   useEffect(() => {
+    // Skip if disabled
+    if (!enabled) {
+      return;
+    }
+
     // Skip if backend already running
     if (tauriBackendService.isBackendRunning()) {
       void checkHealth();
@@ -36,5 +42,5 @@ export function useBackendInitializer() {
     if (status !== 'healthy' && status !== 'starting') {
       void initializeBackend();
     }
-  }, [status, backendUrl, checkHealth]);
+  }, [enabled, status, backendUrl, checkHealth]);
 }
diff --git a/frontend/src/desktop/hooks/useEndpointConfig.ts b/frontend/src/desktop/hooks/useEndpointConfig.ts
index 2a8629ffd..8ccdc66e2 100644
--- a/frontend/src/desktop/hooks/useEndpointConfig.ts
+++ b/frontend/src/desktop/hooks/useEndpointConfig.ts
@@ -1,9 +1,10 @@
-import { useMemo, useState, useEffect, useCallback, useRef } from 'react';
+import { useState, useEffect, useCallback, useRef } from 'react';
 import { isAxiosError } from 'axios';
 import { useTranslation } from 'react-i18next';
 import apiClient from '@app/services/apiClient';
 import { tauriBackendService } from '@app/services/tauriBackendService';
 import { isBackendNotReadyError } from '@app/constants/backendErrors';
+import { connectionModeService } from '@desktop/services/connectionModeService';
 
 interface EndpointConfig {
   backendUrl: string;
@@ -235,17 +236,34 @@ export function useMultipleEndpointsEnabled(endpoints: string[]): {
   };
 }
 
+// Default backend URL from environment variables
+const DEFAULT_BACKEND_URL =
+  import.meta.env.VITE_DESKTOP_BACKEND_URL
+  || import.meta.env.VITE_API_BASE_URL
+  || '';
+
 /**
- * Desktop override exposing the backend URL used by the embedded server.
+ * Desktop override exposing the backend URL based on connection mode.
+ * - Offline mode: Uses local bundled backend (from env vars)
+ * - Server mode: Uses configured server URL from connection config
  */
 export function useEndpointConfig(): EndpointConfig {
-  const backendUrl = useMemo(() => {
-    const runtimeEnv = typeof process !== 'undefined' ? process.env : undefined;
+  const [backendUrl, setBackendUrl] = useState<string>(DEFAULT_BACKEND_URL);
 
-    return runtimeEnv?.STIRLING_BACKEND_URL
-      || import.meta.env.VITE_DESKTOP_BACKEND_URL
-      || import.meta.env.VITE_API_BASE_URL
-      || 'http://localhost:8080';
+  useEffect(() => {
+    connectionModeService.getCurrentConfig()
+      .then((config) => {
+        if (config.mode === 'server' && config.server_config?.url) {
+          setBackendUrl(config.server_config.url);
+        } else {
+          // Offline mode - use default from env vars
+          setBackendUrl(DEFAULT_BACKEND_URL);
+        }
+      })
+      .catch((err) => {
+        console.error('Failed to get connection config:', err);
+        // Keep current URL on error
+      });
   }, []);
 
   return { backendUrl };
diff --git a/frontend/src/desktop/hooks/useFirstLaunchCheck.ts b/frontend/src/desktop/hooks/useFirstLaunchCheck.ts
new file mode 100644
index 000000000..641fe5bfc
--- /dev/null
+++ b/frontend/src/desktop/hooks/useFirstLaunchCheck.ts
@@ -0,0 +1,44 @@
+import { useEffect, useRef, useState } from 'react';
+import { connectionModeService } from '@app/services/connectionModeService';
+import { authService } from '@app/services/authService';
+
+/**
+ * First launch check hook
+ * Checks if this is the first time the app is being launched
+ * Does not require FileContext - can be used early in the provider hierarchy
+ */
+export function useFirstLaunchCheck(): { isFirstLaunch: boolean; setupComplete: boolean } {
+  const [isFirstLaunch, setIsFirstLaunch] = useState(false);
+  const [setupComplete, setSetupComplete] = useState(false);
+  const setupCheckCompleteRef = useRef(false);
+
+  // Check if this is first launch
+  useEffect(() => {
+    const checkFirstLaunch = async () => {
+      try {
+        const firstLaunch = await connectionModeService.isFirstLaunch();
+        setIsFirstLaunch(firstLaunch);
+
+        if (!firstLaunch) {
+          // Not first launch - initialize auth state
+          await authService.initializeAuthState();
+          setSetupComplete(true);
+        }
+
+        setupCheckCompleteRef.current = true;
+      } catch (error) {
+        console.error('Failed to check first launch:', error);
+        // On error, assume not first launch and proceed
+        setIsFirstLaunch(false);
+        setSetupComplete(true);
+        setupCheckCompleteRef.current = true;
+      }
+    };
+
+    if (!setupCheckCompleteRef.current) {
+      checkFirstLaunch();
+    }
+  }, []);
+
+  return { isFirstLaunch, setupComplete };
+}
diff --git a/frontend/src/desktop/services/apiClient.ts b/frontend/src/desktop/services/apiClient.ts
new file mode 100644
index 000000000..8773afc5e
--- /dev/null
+++ b/frontend/src/desktop/services/apiClient.ts
@@ -0,0 +1,34 @@
+/**
+ * Desktop-specific API client using Tauri's native HTTP client
+ * This file overrides @core/services/apiClient.ts for desktop builds
+ * Bypasses CORS restrictions by using native HTTP instead of browser fetch
+ */
+
+import type { AxiosInstance } from 'axios';
+import { create } from '@app/services/tauriHttpClient';
+import { handleHttpError } from '@app/services/httpErrorHandler';
+import { setupApiInterceptors } from '@app/services/apiClientSetup';
+import { getApiBaseUrl } from '@app/services/apiClientConfig';
+
+// Create Tauri HTTP client with default config
+const apiClient = create({
+  baseURL: getApiBaseUrl(),
+  responseType: 'json',
+  withCredentials: true,
+});
+
+// Setup interceptors (desktop-specific auth and backend ready checks)
+// Cast to AxiosInstance - Tauri client has compatible API
+setupApiInterceptors(apiClient as unknown as AxiosInstance);
+
+// ---------- Install error interceptor ----------
+apiClient.interceptors.response.use(
+  (response) => response,
+  async (error) => {
+    await handleHttpError(error); // Handle error (shows toast unless suppressed)
+    return Promise.reject(error);
+  }
+);
+
+// ---------- Exports ----------
+export default apiClient;
diff --git a/frontend/src/desktop/services/apiClientConfig.ts b/frontend/src/desktop/services/apiClientConfig.ts
index 3dfe2a4a7..c823f24e2 100644
--- a/frontend/src/desktop/services/apiClientConfig.ts
+++ b/frontend/src/desktop/services/apiClientConfig.ts
@@ -2,16 +2,19 @@ import { isTauri } from '@tauri-apps/api/core';
 
 /**
  * Desktop override: Determine base URL depending on Tauri environment
+ *
+ * Note: In Tauri mode, the actual URL is determined dynamically by operationRouter
+ * based on connection mode and backend port. This initial baseURL is overridden
+ * by request interceptors in apiClientSetup.ts.
  */
 export function getApiBaseUrl(): string {
   if (!isTauri()) {
     return import.meta.env.VITE_API_BASE_URL || '/';
   }
 
-  if (import.meta.env.DEV) {
-    // During tauri dev we rely on Vite proxy, so use relative path to avoid CORS preflight
-    return '/';
-  }
-
-  return import.meta.env.VITE_DESKTOP_BACKEND_URL || 'http://localhost:8080';
+  // In Tauri mode, return empty string as placeholder
+  // The actual URL will be set dynamically by operationRouter based on:
+  // - Offline mode: dynamic port from tauriBackendService
+  // - Server mode: configured server URL from connectionModeService
+  return '';
 }
diff --git a/frontend/src/desktop/services/apiClientSetup.ts b/frontend/src/desktop/services/apiClientSetup.ts
index eea7521a6..2ba6c5497 100644
--- a/frontend/src/desktop/services/apiClientSetup.ts
+++ b/frontend/src/desktop/services/apiClientSetup.ts
@@ -1,44 +1,134 @@
-import { AxiosInstance } from 'axios';
+import type { AxiosInstance, InternalAxiosRequestConfig } from 'axios';
 import { alert } from '@app/components/toast';
 import { setupApiInterceptors as coreSetup } from '@core/services/apiClientSetup';
 import { tauriBackendService } from '@app/services/tauriBackendService';
 import { createBackendNotReadyError } from '@app/constants/backendErrors';
+import { operationRouter } from '@app/services/operationRouter';
+import { authService } from '@app/services/authService';
+import { connectionModeService } from '@app/services/connectionModeService';
 import i18n from '@app/i18n';
 
 const BACKEND_TOAST_COOLDOWN_MS = 4000;
 let lastBackendToast = 0;
 
+// Extended config for custom properties
+interface ExtendedRequestConfig extends InternalAxiosRequestConfig {
+  operationName?: string;
+  skipBackendReadyCheck?: boolean;
+  _retry?: boolean;
+}
+
 /**
  * Desktop-specific API interceptors
  * - Reuses the core interceptors
- * - Blocks API calls while the bundled backend is still starting and shows
- *   a friendly toast for user-initiated requests (non-GET)
+ * - Dynamically sets base URL based on connection mode
+ * - Adds auth token for remote server requests
+ * - Blocks API calls while the bundled backend is still starting
+ * - Handles auth token refresh on 401 errors
  */
 export function setupApiInterceptors(client: AxiosInstance): void {
   coreSetup(client);
 
+  // Request interceptor: Set base URL and auth headers dynamically
   client.interceptors.request.use(
-    (config) => {
-      const skipCheck = config?.skipBackendReadyCheck === true;
-      if (skipCheck || tauriBackendService.isBackendHealthy()) {
-        return config;
+    async (config: InternalAxiosRequestConfig) => {
+      const extendedConfig = config as ExtendedRequestConfig;
+
+      // Get the operation name from config if provided
+      const operation = extendedConfig.operationName;
+
+      // Get the appropriate base URL for this operation
+      const baseUrl = await operationRouter.getBaseUrl(operation);
+
+      // Build the full URL
+      if (extendedConfig.url && !extendedConfig.url.startsWith('http')) {
+        extendedConfig.url = `${baseUrl}${extendedConfig.url}`;
       }
 
-      const method = (config.method || 'get').toLowerCase();
-      if (method !== 'get') {
-        const now = Date.now();
-        if (now - lastBackendToast > BACKEND_TOAST_COOLDOWN_MS) {
-          lastBackendToast = now;
-          alert({
-            alertType: 'error',
-            title: i18n.t('backendHealth.offline', 'Backend Offline'),
-            body: i18n.t('backendHealth.wait', 'Please wait for the backend to finish launching and try again.'),
-            isPersistentPopup: false,
-          });
+      // Debug logging
+      console.debug(`[apiClientSetup] Request to: ${extendedConfig.url}`);
+
+      // Add auth token for remote requests
+      const isRemote = await operationRouter.isRemoteMode();
+      if (isRemote) {
+        const token = await authService.getAuthToken();
+        if (token) {
+          extendedConfig.headers.Authorization = `Bearer ${token}`;
         }
       }
 
-      return Promise.reject(createBackendNotReadyError());
+      // Backend readiness check (for local backend)
+      const skipCheck = extendedConfig.skipBackendReadyCheck === true;
+      const isOffline = await operationRouter.isOfflineMode();
+
+      if (isOffline && !skipCheck && !tauriBackendService.isBackendHealthy()) {
+        const method = (extendedConfig.method || 'get').toLowerCase();
+        if (method !== 'get') {
+          const now = Date.now();
+          if (now - lastBackendToast > BACKEND_TOAST_COOLDOWN_MS) {
+            lastBackendToast = now;
+            alert({
+              alertType: 'error',
+              title: i18n.t('backendHealth.offline', 'Backend Offline'),
+              body: i18n.t('backendHealth.wait', 'Please wait for the backend to finish launching and try again.'),
+              isPersistentPopup: false,
+            });
+          }
+        }
+        return Promise.reject(createBackendNotReadyError());
+      }
+
+      return extendedConfig;
+    },
+    (error) => Promise.reject(error)
+  );
+
+  // Response interceptor: Handle auth errors
+  client.interceptors.response.use(
+    (response) => response,
+    async (error) => {
+      const originalRequest = error.config as ExtendedRequestConfig;
+
+      // Handle 401 Unauthorized - try to refresh token
+      if (error.response?.status === 401 && !originalRequest._retry) {
+        originalRequest._retry = true;
+
+        const isRemote = await operationRouter.isRemoteMode();
+        if (isRemote) {
+          const serverConfig = await connectionModeService.getServerConfig();
+          if (serverConfig) {
+            const refreshed = await authService.refreshToken(serverConfig.url);
+            if (refreshed) {
+              // Retry the original request with new token
+              const token = await authService.getAuthToken();
+              if (token) {
+                originalRequest.headers.Authorization = `Bearer ${token}`;
+              }
+              return client(originalRequest);
+            }
+          }
+        }
+
+        // Refresh failed or not in remote mode - user needs to login again
+        alert({
+          alertType: 'error',
+          title: i18n.t('auth.sessionExpired', 'Session Expired'),
+          body: i18n.t('auth.pleaseLoginAgain', 'Please login again.'),
+          isPersistentPopup: false,
+        });
+      }
+
+      // Handle 403 Forbidden - unauthorized access
+      if (error.response?.status === 403) {
+        alert({
+          alertType: 'error',
+          title: i18n.t('auth.accessDenied', 'Access Denied'),
+          body: i18n.t('auth.insufficientPermissions', 'You do not have permission to perform this action.'),
+          isPersistentPopup: false,
+        });
+      }
+
+      return Promise.reject(error);
     }
   );
 }
diff --git a/frontend/src/desktop/services/authService.ts b/frontend/src/desktop/services/authService.ts
new file mode 100644
index 000000000..65d0c4cce
--- /dev/null
+++ b/frontend/src/desktop/services/authService.ts
@@ -0,0 +1,198 @@
+import { invoke } from '@tauri-apps/api/core';
+import axios from 'axios';
+
+export interface UserInfo {
+  username: string;
+  email?: string;
+}
+
+interface LoginResponse {
+  token: string;
+  username: string;
+  email: string | null;
+}
+
+export type AuthStatus = 'authenticated' | 'unauthenticated' | 'refreshing';
+
+export class AuthService {
+  private static instance: AuthService;
+  private authStatus: AuthStatus = 'unauthenticated';
+  private userInfo: UserInfo | null = null;
+  private authListeners = new Set<(status: AuthStatus, userInfo: UserInfo | null) => void>();
+
+  static getInstance(): AuthService {
+    if (!AuthService.instance) {
+      AuthService.instance = new AuthService();
+    }
+    return AuthService.instance;
+  }
+
+  subscribeToAuth(listener: (status: AuthStatus, userInfo: UserInfo | null) => void): () => void {
+    this.authListeners.add(listener);
+    // Immediately notify new listener of current state
+    listener(this.authStatus, this.userInfo);
+    return () => {
+      this.authListeners.delete(listener);
+    };
+  }
+
+  private notifyListeners() {
+    this.authListeners.forEach(listener => listener(this.authStatus, this.userInfo));
+  }
+
+  private setAuthStatus(status: AuthStatus, userInfo: UserInfo | null = null) {
+    this.authStatus = status;
+    this.userInfo = userInfo;
+    this.notifyListeners();
+  }
+
+  async login(serverUrl: string, username: string, password: string): Promise<UserInfo> {
+    try {
+      console.log('Logging in to:', serverUrl);
+
+      // Call Rust login command (bypasses CORS)
+      const response = await invoke<LoginResponse>('login', {
+        serverUrl,
+        username,
+        password,
+      });
+
+      const { token, username: returnedUsername, email } = response;
+
+      // Save the token to keyring
+      await invoke('save_auth_token', { token });
+
+      // Save user info to store
+      await invoke('save_user_info', {
+        username: returnedUsername || username,
+        email,
+      });
+
+      const userInfo: UserInfo = {
+        username: returnedUsername || username,
+        email: email || undefined,
+      };
+
+      this.setAuthStatus('authenticated', userInfo);
+
+      console.log('Login successful');
+      return userInfo;
+    } catch (error) {
+      console.error('Login failed:', error);
+      this.setAuthStatus('unauthenticated', null);
+
+      // Rust commands return string errors
+      if (typeof error === 'string') {
+        throw new Error(error);
+      }
+
+      throw new Error('Login failed. Please try again.');
+    }
+  }
+
+  async logout(): Promise<void> {
+    try {
+      console.log('Logging out');
+
+      // Clear token from keyring
+      await invoke('clear_auth_token');
+
+      // Clear user info from store
+      await invoke('clear_user_info');
+
+      this.setAuthStatus('unauthenticated', null);
+
+      console.log('Logged out successfully');
+    } catch (error) {
+      console.error('Error during logout:', error);
+      // Still set status to unauthenticated even if clear fails
+      this.setAuthStatus('unauthenticated', null);
+    }
+  }
+
+  async getAuthToken(): Promise<string | null> {
+    try {
+      const token = await invoke<string | null>('get_auth_token');
+      return token || null;
+    } catch (error) {
+      console.error('Failed to get auth token:', error);
+      return null;
+    }
+  }
+
+  async isAuthenticated(): Promise<boolean> {
+    const token = await this.getAuthToken();
+    return token !== null;
+  }
+
+  async getUserInfo(): Promise<UserInfo | null> {
+    if (this.userInfo) {
+      return this.userInfo;
+    }
+
+    try {
+      const userInfo = await invoke<UserInfo | null>('get_user_info');
+      this.userInfo = userInfo;
+      return userInfo;
+    } catch (error) {
+      console.error('Failed to get user info:', error);
+      return null;
+    }
+  }
+
+  async refreshToken(serverUrl: string): Promise<boolean> {
+    try {
+      console.log('Refreshing auth token');
+      this.setAuthStatus('refreshing', this.userInfo);
+
+      const currentToken = await this.getAuthToken();
+      if (!currentToken) {
+        this.setAuthStatus('unauthenticated', null);
+        return false;
+      }
+
+      // Call the server's refresh endpoint
+      const response = await axios.post(
+        `${serverUrl}/api/v1/auth/refresh`,
+        {},
+        {
+          headers: {
+            Authorization: `Bearer ${currentToken}`,
+          },
+        }
+      );
+
+      const { token } = response.data;
+
+      // Save the new token
+      await invoke('save_auth_token', { token });
+
+      const userInfo = await this.getUserInfo();
+      this.setAuthStatus('authenticated', userInfo);
+
+      console.log('Token refreshed successfully');
+      return true;
+    } catch (error) {
+      console.error('Token refresh failed:', error);
+      this.setAuthStatus('unauthenticated', null);
+
+      // Clear stored credentials on refresh failure
+      await this.logout();
+
+      return false;
+    }
+  }
+
+  async initializeAuthState(): Promise<void> {
+    const token = await this.getAuthToken();
+    const userInfo = await this.getUserInfo();
+
+    if (token && userInfo) {
+      this.setAuthStatus('authenticated', userInfo);
+    } else {
+      this.setAuthStatus('unauthenticated', null);
+    }
+  }
+}
+
+export const authService = AuthService.getInstance();
diff --git a/frontend/src/desktop/services/connectionModeService.ts b/frontend/src/desktop/services/connectionModeService.ts
new file mode 100644
index 000000000..f1a96c9c5
--- /dev/null
+++ b/frontend/src/desktop/services/connectionModeService.ts
@@ -0,0 +1,131 @@
+import { invoke } from '@tauri-apps/api/core';
+import { fetch } from '@tauri-apps/plugin-http';
+
+export type ConnectionMode = 'offline' | 'server';
+export type ServerType = 'saas' | 'selfhosted';
+
+export interface ServerConfig {
+  url: string;
+  server_type: ServerType;
+}
+
+export interface ConnectionConfig {
+  mode: ConnectionMode;
+  server_config: ServerConfig | null;
+}
+
+export class ConnectionModeService {
+  private static instance: ConnectionModeService;
+  private currentConfig: ConnectionConfig | null = null;
+  private configLoadedOnce = false;
+  private modeListeners = new Set<(config: ConnectionConfig) => void>();
+
+  static getInstance(): ConnectionModeService {
+    if (!ConnectionModeService.instance) {
+      ConnectionModeService.instance = new ConnectionModeService();
+    }
+    return ConnectionModeService.instance;
+  }
+
+  async getCurrentConfig(): Promise<ConnectionConfig> {
+    if (!this.configLoadedOnce) {
+      await this.loadConfig();
+    }
+    return this.currentConfig || { mode: 'offline', server_config: null };
+  }
+
+  async getCurrentMode(): Promise<ConnectionMode> {
+    const config = await this.getCurrentConfig();
+    return config.mode;
+  }
+
+  async getServerConfig(): Promise<ServerConfig | null> {
+    const config = await this.getCurrentConfig();
+    return config.server_config;
+  }
+
+  subscribeToModeChanges(listener: (config: ConnectionConfig) => void): () => void {
+    this.modeListeners.add(listener);
+    return () => {
+      this.modeListeners.delete(listener);
+    };
+  }
+
+  private notifyListeners() {
+    if (this.currentConfig) {
+      this.modeListeners.forEach(listener => listener(this.currentConfig!));
+    }
+  }
+
+  private async loadConfig(): Promise<void> {
+    try {
+      const config = await invoke<ConnectionConfig>('get_connection_config');
+      this.currentConfig = config;
+      this.configLoadedOnce = true;
+    } catch (error) {
+      console.error('Failed to load connection config:', error);
+      // Default to offline mode on error
+      this.currentConfig = { mode: 'offline', server_config: null };
+      this.configLoadedOnce = true;
+    }
+  }
+
+  async switchToOffline(): Promise<void> {
+    console.log('Switching to offline mode');
+
+    await invoke('set_connection_mode', {
+      mode: 'offline',
+      serverConfig: null,
+    });
+
+    this.currentConfig = { mode: 'offline', server_config: null };
+    this.notifyListeners();
+
+    console.log('Switched to offline mode successfully');
+  }
+
+  async switchToServer(serverConfig: ServerConfig): Promise<void> {
+    console.log('Switching to server mode:', serverConfig);
+
+    await invoke('set_connection_mode', {
+      mode: 'server',
+      serverConfig,
+    });
+
+    this.currentConfig = { mode: 'server', server_config: serverConfig };
+    this.notifyListeners();
+
+    console.log('Switched to server mode successfully');
+  }
+
+  async testConnection(url: string): Promise<boolean> {
+    console.log(`[ConnectionModeService] Testing connection to: ${url}`);
+    try {
+      // Test connection by hitting the health/status endpoint
+      const healthUrl = `${url.replace(/\/$/, '')}/api/v1/info/status`;
+      const response = await fetch(healthUrl, {
+        method: 'GET',
+        connectTimeout: 10000,
+      });
+
+      const isOk = response.ok;
+      console.log(`[ConnectionModeService] Server connection test result: ${isOk}`);
+      return isOk;
+    } catch (error) {
+      console.warn('[ConnectionModeService] Server connection test failed:', error);
+      return false;
+    }
+  }
+
+  async isFirstLaunch(): Promise<boolean> {
+    try {
+      const result = await invoke<boolean>('is_first_launch');
+      return result;
+    } catch (error) {
+      console.error('Failed to check first launch:', error);
+      return false;
+    }
+  }
+}
+
+export const connectionModeService = ConnectionModeService.getInstance();
diff --git a/frontend/src/desktop/services/operationRouter.ts b/frontend/src/desktop/services/operationRouter.ts
new file mode 100644
index 000000000..723878b97
--- /dev/null
+++ b/frontend/src/desktop/services/operationRouter.ts
@@ -0,0 +1,99 @@
+import { connectionModeService } from '@app/services/connectionModeService';
+import { tauriBackendService } from '@app/services/tauriBackendService';
+
+export type ExecutionTarget = 'local' | 'remote';
+
+export class OperationRouter {
+  private static instance: OperationRouter;
+
+  static getInstance(): OperationRouter {
+    if (!OperationRouter.instance) {
+      OperationRouter.instance = new OperationRouter();
+    }
+    return OperationRouter.instance;
+  }
+
+  /**
+   * Determines where an operation should execute
+   * @param _operation - The operation name (for future operation classification)
+   * @returns 'local' or 'remote'
+   */
+  async getExecutionTarget(_operation?: string): Promise<ExecutionTarget> {
+    const mode = await connectionModeService.getCurrentMode();
+
+    // Current implementation: simple mode-based routing
+    if (mode === 'offline') {
+      return 'local';
+    }
+
+    // In server mode, currently all operations go to remote
+    // Future enhancement: check if operation is "simple" and route to local if so
+    // Example future logic:
+    // if (mode === 'server' && operation && this.isSimpleOperation(operation)) {
+    //   return 'local';
+    // }
+
+    return 'remote';
+  }
+
+  /**
+   * Gets the base URL for an operation based on execution target
+   * @param _operation - The operation name (for future operation classification)
+   * @returns Base URL for API calls
+   */
+  async getBaseUrl(_operation?: string): Promise<string> {
+    const target = await this.getExecutionTarget(_operation);
+
+    if (target === 'local') {
+      // Use dynamically assigned port from backend service
+      const backendUrl = tauriBackendService.getBackendUrl();
+      if (!backendUrl) {
+        throw new Error('Backend URL not available - backend may still be starting');
+      }
+      // Strip trailing slash to avoid double slashes in URLs
+      return backendUrl.replace(/\/$/, '');
+    }
+
+    // Remote: get from server config
+    const serverConfig = await connectionModeService.getServerConfig();
+    if (!serverConfig) {
+      console.warn('No server config found');
+      throw new Error('Server configuration not found');
+    }
+
+    // Strip trailing slash to avoid double slashes in URLs
+    return serverConfig.url.replace(/\/$/, '');
+  }
+
+  /**
+   * Checks if we're currently in remote mode
+   */
+  async isRemoteMode(): Promise<boolean> {
+    const mode = await connectionModeService.getCurrentMode();
+    return mode === 'server';
+  }
+
+  /**
+   * Checks if we're currently in offline mode
+   */
+  async isOfflineMode(): Promise<boolean> {
+    const mode = await connectionModeService.getCurrentMode();
+    return mode === 'offline';
+  }
+
+  // Future enhancement: operation classification
+  // private isSimpleOperation(operation: string): boolean {
+  //   const simpleOperations = [
+  //     'rotate',
+  //     'merge',
+  //     'split',
+  //     'extract-pages',
+  //     'remove-pages',
+  //     'reorder-pages',
+  //     'metadata',
+  //   ];
+  //   return simpleOperations.includes(operation);
+  // }
+}
+
+export const operationRouter = OperationRouter.getInstance();
diff --git a/frontend/src/desktop/services/tauriBackendService.ts b/frontend/src/desktop/services/tauriBackendService.ts
index 2a2ee6cef..ce8bd9336 100644
--- a/frontend/src/desktop/services/tauriBackendService.ts
+++ b/frontend/src/desktop/services/tauriBackendService.ts
@@ -1,4 +1,6 @@
 import { invoke } from '@tauri-apps/api/core';
+import { fetch } from '@tauri-apps/plugin-http';
+import { connectionModeService } from '@app/services/connectionModeService';
 
 export type BackendStatus = 'stopped' | 'starting' | 'healthy' | 'unhealthy';
 
@@ -6,6 +8,7 @@ export class TauriBackendService {
   private static instance: TauriBackendService;
   private backendStarted = false;
   private backendStatus: BackendStatus = 'stopped';
+  private backendPort: number | null = null;
   private healthMonitor: Promise<void> | null = null;
   private startPromise: Promise<void> | null = null;
   private statusListeners = new Set<(status: BackendStatus) => void>();
@@ -29,6 +32,14 @@ export class TauriBackendService {
     return this.backendStatus === 'healthy';
   }
 
+  getBackendPort(): number | null {
+    return this.backendPort;
+  }
+
+  getBackendUrl(): string | null {
+    return this.backendPort ? `http://localhost:${this.backendPort}` : null;
+  }
+
   subscribeToStatus(listener: (status: BackendStatus) => void): () => void {
     this.statusListeners.add(listener);
     return () => {
@@ -44,6 +55,21 @@ export class TauriBackendService {
     this.statusListeners.forEach(listener => listener(status));
   }
 
+  /**
+   * Initialize health monitoring for an external server (server mode)
+   * Does not start bundled backend, but enables health checks
+   */
+  async initializeExternalBackend(): Promise<void> {
+    if (this.backendStarted) {
+      return;
+    }
+
+    console.log('[TauriBackendService] Initializing external backend monitoring');
+    this.backendStarted = true; // Mark as active for health checks
+    this.setStatus('starting');
+    this.beginHealthMonitoring();
+  }
+
   async startBackend(backendUrl?: string): Promise<void> {
     if (this.backendStarted) {
       return;
@@ -56,10 +82,14 @@ export class TauriBackendService {
     this.setStatus('starting');
 
     this.startPromise = invoke('start_backend', { backendUrl })
-      .then((result) => {
+      .then(async (result) => {
         console.log('Backend started:', result);
         this.backendStarted = true;
         this.setStatus('starting');
+
+        // Poll for the dynamically assigned port
+        await this.waitForPort();
+
         this.beginHealthMonitoring();
       })
       .catch((error) => {
@@ -74,6 +104,24 @@ export class TauriBackendService {
     return this.startPromise;
   }
 
+  private async waitForPort(maxAttempts = 30): Promise<void> {
+    console.log('[TauriBackendService] Waiting for backend port assignment...');
+    for (let i = 0; i < maxAttempts; i++) {
+      try {
+        const port = await invoke<number | null>('get_backend_port');
+        if (port) {
+          this.backendPort = port;
+          console.log(`[TauriBackendService] Backend port detected: ${port}`);
+          return;
+        }
+      } catch (error) {
+        console.error('Failed to get backend port:', error);
+      }
+      await new Promise(resolve => setTimeout(resolve, 500));
+    }
+    throw new Error('Failed to detect backend port after 15 seconds');
+  }
+
   private beginHealthMonitoring() {
     if (this.healthMonitor) {
       return;
@@ -88,16 +136,58 @@ export class TauriBackendService {
   }
 
   async checkBackendHealth(): Promise<boolean> {
+    const mode = await connectionModeService.getCurrentMode();
+
+    // For remote server mode, check the configured server
+    if (mode !== 'offline') {
+      const serverConfig = await connectionModeService.getServerConfig();
+      if (!serverConfig) {
+        console.error('[TauriBackendService] Server mode but no server URL configured');
+        this.setStatus('unhealthy');
+        return false;
+      }
+
+      try {
+        const baseUrl = serverConfig.url.replace(/\/$/, '');
+        const healthUrl = `${baseUrl}/api/v1/info/status`;
+        const response = await fetch(healthUrl, {
+          method: 'GET',
+          connectTimeout: 5000,
+        });
+
+        const isHealthy = response.ok;
+        this.setStatus(isHealthy ? 'healthy' : 'unhealthy');
+        return isHealthy;
+      } catch (error) {
+        const errorStr = String(error);
+        if (!errorStr.includes('connection refused') && !errorStr.includes('No connection could be made')) {
+          console.error('[TauriBackendService] Server health check failed:', error);
+        }
+        this.setStatus('unhealthy');
+        return false;
+      }
+    }
+
+    // For offline mode, check the bundled backend via Rust
     if (!this.backendStarted) {
       this.setStatus('stopped');
       return false;
     }
+
+    if (!this.backendPort) {
+      console.debug('[TauriBackendService] Backend port not available yet');
+      return false;
+    }
+
     try {
-      const isHealthy = await invoke<boolean>('check_backend_health');
+      const isHealthy = await invoke<boolean>('check_backend_health', { port: this.backendPort });
       this.setStatus(isHealthy ? 'healthy' : 'unhealthy');
       return isHealthy;
     } catch (error) {
-      console.error('Health check failed:', error);
+      const errorStr = String(error);
+      if (!errorStr.includes('connection refused') && !errorStr.includes('No connection could be made')) {
+        console.error('[TauriBackendService] Bundled backend health check failed:', error);
+      }
       this.setStatus('unhealthy');
       return false;
     }
@@ -115,6 +205,18 @@ export class TauriBackendService {
     this.setStatus('unhealthy');
     throw new Error('Backend failed to become healthy after 60 seconds');
   }
+
+  /**
+   * Reset backend state (used when switching from external to local backend)
+   */
+  reset(): void {
+    console.log('[TauriBackendService] Resetting backend state');
+    this.backendStarted = false;
+    this.backendPort = null;
+    this.setStatus('stopped');
+    this.healthMonitor = null;
+    this.startPromise = null;
+  }
 }
 
 export const tauriBackendService = TauriBackendService.getInstance();
diff --git a/frontend/src/desktop/services/tauriHttpClient.ts b/frontend/src/desktop/services/tauriHttpClient.ts
new file mode 100644
index 000000000..89c87bfbb
--- /dev/null
+++ b/frontend/src/desktop/services/tauriHttpClient.ts
@@ -0,0 +1,361 @@
+import { fetch } from '@tauri-apps/plugin-http';
+
+/**
+ * Tauri HTTP Client - wrapper around Tauri's native HTTP client
+ * Provides axios-compatible API while bypassing CORS restrictions
+ */
+
+export interface TauriHttpResponse<T = any> {
+  data: T;
+  status: number;
+  statusText: string;
+  headers: Record<string, string>;
+  config: TauriHttpRequestConfig;
+}
+
+export interface TauriHttpRequestConfig {
+  url?: string;
+  method?: string;
+  baseURL?: string;
+  headers?: Record<string, string>;
+  params?: Record<string, string | number | boolean> | any;
+  data?: any;
+  timeout?: number;
+  responseType?: 'json' | 'text' | 'blob' | 'arraybuffer';
+  withCredentials?: boolean;
+  // Custom properties for desktop
+  operationName?: string;
+  skipBackendReadyCheck?: boolean;
+  // Axios compatibility properties (ignored by Tauri HTTP)
+  suppressErrorToast?: boolean;
+  cancelToken?: any;
+}
+
+export interface TauriHttpError extends Error {
+  config?: TauriHttpRequestConfig;
+  code?: string;
+  request?: unknown;
+  response?: TauriHttpResponse;
+  isAxiosError: boolean;
+  toJSON: () => object;
+}
+
+type RequestInterceptor = (config: TauriHttpRequestConfig) => Promise<TauriHttpRequestConfig> | TauriHttpRequestConfig;
+type ResponseInterceptor<T = any> = (response: TauriHttpResponse<T>) => Promise<TauriHttpResponse<T>> | TauriHttpResponse<T>;
+type ErrorInterceptor = (error: any) => Promise<any>;
+
+interface Interceptors {
+  request: {
+    handlers: RequestInterceptor[];
+    use: (onFulfilled: RequestInterceptor, onRejected?: ErrorInterceptor) => number;
+  };
+  response: {
+    handlers: { fulfilled: ResponseInterceptor; rejected?: ErrorInterceptor }[];
+    use: (onFulfilled: ResponseInterceptor, onRejected?: ErrorInterceptor) => number;
+  };
+}
+
+class TauriHttpClient {
+  public defaults: TauriHttpRequestConfig = {
+    baseURL: '',
+    headers: {},
+    timeout: 120000,
+    responseType: 'json',
+    withCredentials: true,
+  };
+
+  public interceptors: Interceptors = {
+    request: {
+      handlers: [],
+      use: (onFulfilled: RequestInterceptor, _onRejected?: ErrorInterceptor) => {
+        this.interceptors.request.handlers.push(onFulfilled);
+        return this.interceptors.request.handlers.length - 1;
+      },
+    },
+    response: {
+      handlers: [],
+      use: (onFulfilled: ResponseInterceptor, onRejected?: ErrorInterceptor) => {
+        this.interceptors.response.handlers.push({ fulfilled: onFulfilled, rejected: onRejected });
+        return this.interceptors.response.handlers.length - 1;
+      },
+    },
+  };
+
+  constructor(config?: TauriHttpRequestConfig) {
+    if (config) {
+      this.defaults = { ...this.defaults, ...config };
+    }
+  }
+
+  private createError(message: string, config?: TauriHttpRequestConfig, code?: string, response?: TauriHttpResponse): TauriHttpError {
+    const error = new Error(message) as TauriHttpError;
+    error.config = config;
+    error.code = code;
+    error.response = response;
+    error.isAxiosError = true;
+    error.toJSON = () => ({
+      message: error.message,
+      name: error.name,
+      config: error.config,
+      code: error.code,
+    });
+    return error;
+  }
+
+  private buildUrl(config: TauriHttpRequestConfig): string {
+    let url = config.url || '';
+
+    // If URL is already absolute, use it as-is
+    if (url.startsWith('http://') || url.startsWith('https://')) {
+      return url;
+    }
+
+    // Prepend baseURL if present
+    const baseURL = config.baseURL || this.defaults.baseURL || '';
+    if (baseURL) {
+      url = baseURL + url;
+    }
+
+    // Add query parameters
+    if (config.params && typeof config.params === 'object') {
+      const searchParams = new URLSearchParams();
+      Object.entries(config.params as Record<string, unknown>).forEach(([key, value]) => {
+        if (value !== null && value !== undefined) {
+          searchParams.append(key, String(value));
+        }
+      });
+      const queryString = searchParams.toString();
+      if (queryString) {
+        url += (url.includes('?') ? '&' : '?') + queryString;
+      }
+    }
+
+    return url;
+  }
+
+  private async executeRequest<T = any>(config: TauriHttpRequestConfig): Promise<TauriHttpResponse<T>> {
+    // Merge with defaults
+    const mergedConfig: TauriHttpRequestConfig = {
+      ...this.defaults,
+      ...config,
+      headers: {
+        ...this.defaults.headers,
+        ...config.headers,
+      },
+    };
+
+    // Run request interceptors
+    let finalConfig = mergedConfig;
+    for (const interceptor of this.interceptors.request.handlers) {
+      finalConfig = await Promise.resolve(interceptor(finalConfig));
+    }
+
+    const url = this.buildUrl(finalConfig);
+    const method = (finalConfig.method || 'GET').toUpperCase();
+
+    // Prepare request body and headers
+    let body: BodyInit | undefined;
+    const headers: Record<string, string> = { ...(finalConfig.headers || {}) };
+
+    if (finalConfig.data) {
+      if (finalConfig.data instanceof FormData) {
+        // FormData can be passed directly
+        body = finalConfig.data;
+      } else if (typeof finalConfig.data === 'object') {
+        // Serialize as JSON
+        body = JSON.stringify(finalConfig.data);
+        if (!headers['Content-Type']) {
+          headers['Content-Type'] = 'application/json';
+        }
+      } else {
+        body = String(finalConfig.data);
+      }
+    }
+
+    try {
+      // Debug logging
+      console.debug(`[tauriHttpClient] Fetch request:`, { url, method });
+
+      // Make the request using Tauri's native HTTP client (standard Fetch API)
+      const response = await fetch(url, {
+        method,
+        headers,
+        body,
+      });
+
+      // Parse response based on responseType
+      let data: T;
+      const responseType = finalConfig.responseType || 'json';
+
+      if (responseType === 'json') {
+        data = await response.json() as T;
+      } else if (responseType === 'text') {
+        data = (await response.text()) as T;
+      } else if (responseType === 'blob') {
+        // Standard fetch doesn't set blob.type from Content-Type header (unlike axios)
+        // Set it manually to match axios behavior
+        const blob = await response.blob();
+        if (!blob.type) {
+          const contentType = response.headers.get('content-type') || 'application/octet-stream';
+          data = new Blob([blob], { type: contentType }) as T;
+        } else {
+          data = blob as T;
+        }
+      } else if (responseType === 'arraybuffer') {
+        data = (await response.arrayBuffer()) as T;
+      } else {
+        data = await response.json() as T;
+      }
+
+      // Convert Headers to plain object
+      const responseHeaders: Record<string, string> = {};
+      response.headers.forEach((value, key) => {
+        responseHeaders[key] = value;
+      });
+
+      const httpResponse: TauriHttpResponse<T> = {
+        data,
+        status: response.status,
+        statusText: response.statusText || '',
+        headers: responseHeaders,
+        config: finalConfig,
+      };
+
+      // Check for HTTP errors
+      if (!response.ok) {
+        const error = this.createError(
+          `Request failed with status code ${response.status}`,
+          finalConfig,
+          'ERR_BAD_REQUEST',
+          httpResponse
+        );
+
+        // Run error interceptors
+        let finalError: unknown = error;
+        for (const handler of this.interceptors.response.handlers) {
+          if (handler.rejected) {
+            try {
+              finalError = await Promise.resolve(handler.rejected(finalError));
+            } catch (e) {
+              finalError = e;
+            }
+          }
+        }
+        throw finalError;
+      }
+
+      // Run response interceptors
+      let finalResponse = httpResponse;
+      for (const handler of this.interceptors.response.handlers) {
+        finalResponse = await Promise.resolve(handler.fulfilled(finalResponse)) as TauriHttpResponse<T>;
+      }
+
+      return finalResponse;
+    } catch (error: unknown) {
+      // If it's already a TauriHttpError with interceptors run, re-throw
+      if (error && typeof error === 'object' && 'isAxiosError' in error) {
+        throw error;
+      }
+
+      // Create new error for network/other failures
+      const errorMessage = error instanceof Error ? error.message : 'Network Error';
+      const httpError = this.createError(
+        errorMessage,
+        finalConfig,
+        'ERR_NETWORK'
+      );
+
+      // Run error interceptors
+      let finalError: unknown = httpError;
+      for (const handler of this.interceptors.response.handlers) {
+        if (handler.rejected) {
+          try {
+            finalError = await Promise.resolve(handler.rejected(finalError));
+          } catch (e) {
+            finalError = e;
+          }
+        }
+      }
+      throw finalError;
+    }
+  }
+
+  async request<T = any>(config: TauriHttpRequestConfig): Promise<TauriHttpResponse<T>> {
+    return this.executeRequest<T>(config);
+  }
+
+  async get<T = any>(url: string, config?: TauriHttpRequestConfig): Promise<TauriHttpResponse<T>> {
+    return this.executeRequest<T>({ ...config, method: 'GET', url });
+  }
+
+  async delete<T = any>(url: string, config?: TauriHttpRequestConfig): Promise<TauriHttpResponse<T>> {
+    return this.executeRequest<T>({ ...config, method: 'DELETE', url });
+  }
+
+  async head<T = any>(url: string, config?: TauriHttpRequestConfig): Promise<TauriHttpResponse<T>> {
+    return this.executeRequest<T>({ ...config, method: 'HEAD', url });
+  }
+
+  async options<T = any>(url: string, config?: TauriHttpRequestConfig): Promise<TauriHttpResponse<T>> {
+    return this.executeRequest<T>({ ...config, method: 'OPTIONS', url });
+  }
+
+  async post<T = any>(url: string, data?: any, config?: TauriHttpRequestConfig): Promise<TauriHttpResponse<T>> {
+    return this.executeRequest<T>({ ...config, method: 'POST', url, data });
+  }
+
+  async put<T = any>(url: string, data?: any, config?: TauriHttpRequestConfig): Promise<TauriHttpResponse<T>> {
+    return this.executeRequest<T>({ ...config, method: 'PUT', url, data });
+  }
+
+  async patch<T = any>(url: string, data?: any, config?: TauriHttpRequestConfig): Promise<TauriHttpResponse<T>> {
+    return this.executeRequest<T>({ ...config, method: 'PATCH', url, data });
+  }
+
+  // Axios compatibility methods
+  create(config?: TauriHttpRequestConfig): TauriHttpClient {
+    return new TauriHttpClient({ ...this.defaults, ...config });
+  }
+
+  getUri(config?: TauriHttpRequestConfig): string {
+    return this.buildUrl({ ...this.defaults, ...config });
+  }
+
+  async postForm<T = any>(url: string, data?: any, config?: TauriHttpRequestConfig): Promise<TauriHttpResponse<T>> {
+    const formData = data instanceof FormData ? data : new FormData();
+    if (!(data instanceof FormData) && data && typeof data === 'object') {
+      Object.entries(data).forEach(([key, value]) => {
+        formData.append(key, String(value));
+      });
+    }
+    return this.post<T>(url, formData, config);
+  }
+
+  async putForm<T = any>(url: string, data?: any, config?: TauriHttpRequestConfig): Promise<TauriHttpResponse<T>> {
+    const formData = data instanceof FormData ? data : new FormData();
+    if (!(data instanceof FormData) && data && typeof data === 'object') {
+      Object.entries(data).forEach(([key, value]) => {
+        formData.append(key, String(value));
+      });
+    }
+    return this.put<T>(url, formData, config);
+  }
+
+  async patchForm<T = any>(url: string, data?: any, config?: TauriHttpRequestConfig): Promise<TauriHttpResponse<T>> {
+    const formData = data instanceof FormData ? data : new FormData();
+    if (!(data instanceof FormData) && data && typeof data === 'object') {
+      Object.entries(data).forEach(([key, value]) => {
+        formData.append(key, String(value));
+      });
+    }
+    return this.patch<T>(url, formData, config);
+  }
+}
+
+// Factory function matching axios.create()
+export function create(config?: TauriHttpRequestConfig): TauriHttpClient {
+  return new TauriHttpClient(config);
+}
+
+// Default instance
+export default new TauriHttpClient();
diff --git a/frontend/src/proprietary/components/AppProviders.tsx b/frontend/src/proprietary/components/AppProviders.tsx
index f0cadfa51..b865e4f26 100644
--- a/frontend/src/proprietary/components/AppProviders.tsx
+++ b/frontend/src/proprietary/components/AppProviders.tsx
@@ -1,5 +1,8 @@
 import { AppProviders as CoreAppProviders, AppProvidersProps } from "@core/components/AppProviders";
 import { AuthProvider } from "@app/auth/UseSession";
+import { LicenseProvider } from "@app/contexts/LicenseContext";
+import { CheckoutProvider } from "@app/contexts/CheckoutContext";
+import UpgradeBanner from "@app/components/shared/UpgradeBanner";
 
 export function AppProviders({ children, appConfigRetryOptions, appConfigProviderProps }: AppProvidersProps) {
   return (
@@ -8,7 +11,12 @@ export function AppProviders({ children, appConfigRetryOptions, appConfigProvide
       appConfigProviderProps={appConfigProviderProps}
     >
       <AuthProvider>
-        {children}
+        <LicenseProvider>
+          <CheckoutProvider>
+            <UpgradeBanner />
+            {children}
+          </CheckoutProvider>
+        </LicenseProvider>
       </AuthProvider>
     </CoreAppProviders>
   );
diff --git a/frontend/src/proprietary/components/shared/ManageBillingButton.tsx b/frontend/src/proprietary/components/shared/ManageBillingButton.tsx
new file mode 100644
index 000000000..fc523f62f
--- /dev/null
+++ b/frontend/src/proprietary/components/shared/ManageBillingButton.tsx
@@ -0,0 +1,53 @@
+import React, { useState } from 'react';
+import { Button } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import licenseService from '@app/services/licenseService';
+import { alert } from '@app/components/toast';
+
+interface ManageBillingButtonProps {
+  returnUrl?: string;
+}
+
+export const ManageBillingButton: React.FC<ManageBillingButtonProps> = ({
+  returnUrl = window.location.href,
+}) => {
+  const { t } = useTranslation();
+  const [loading, setLoading] = useState(false);
+
+  const handleClick = async () => {
+    try {
+      setLoading(true);
+
+      // Get current license key for authentication
+      const licenseInfo = await licenseService.getLicenseInfo();
+
+      if (!licenseInfo.licenseKey) {
+        throw new Error('No license key found. Please activate a license first.');
+      }
+
+      // Create billing portal session with license key
+      const response = await licenseService.createBillingPortalSession(
+        returnUrl,
+        licenseInfo.licenseKey
+      );
+
+      // Open billing portal in new tab
+      window.open(response.url, '_blank');
+      setLoading(false);
+    } catch (error: any) {
+      console.error('Failed to open billing portal:', error);
+      alert({
+        alertType: 'error',
+        title: t('billing.portal.error', 'Failed to open billing portal'),
+        body: error.message || 'Please try again or contact support.',
+      });
+      setLoading(false);
+    }
+  };
+
+  return (
+    <Button variant="outline" onClick={handleClick} loading={loading}>
+      {t('billing.manageBilling', 'Manage Billing')}
+    </Button>
+  );
+};
diff --git a/frontend/src/proprietary/components/shared/StripeCheckout.tsx b/frontend/src/proprietary/components/shared/StripeCheckout.tsx
new file mode 100644
index 000000000..6018dcafc
--- /dev/null
+++ b/frontend/src/proprietary/components/shared/StripeCheckout.tsx
@@ -0,0 +1,507 @@
+import React, { useState, useEffect, useCallback } from 'react';
+import { Modal, Button, Text, Alert, Loader, Stack, Group, Paper, SegmentedControl, Grid, Code } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import { loadStripe } from '@stripe/stripe-js';
+import { EmbeddedCheckoutProvider, EmbeddedCheckout } from '@stripe/react-stripe-js';
+import licenseService, { PlanTierGroup } from '@app/services/licenseService';
+import { Z_INDEX_OVER_CONFIG_MODAL } from '@app/styles/zIndex';
+import { pollLicenseKeyWithBackoff, activateLicenseKey, resyncExistingLicense } from '@app/utils/licenseCheckoutUtils';
+
+// Validate Stripe key (static validation, no dynamic imports)
+const STRIPE_KEY = import.meta.env.VITE_STRIPE_PUBLISHABLE_KEY;
+
+if (!STRIPE_KEY) {
+  console.error(
+    'VITE_STRIPE_PUBLISHABLE_KEY environment variable is required. ' +
+    'Please add it to your .env file. ' +
+    'Get your key from https://dashboard.stripe.com/apikeys'
+  );
+}
+
+if (STRIPE_KEY && !STRIPE_KEY.startsWith('pk_')) {
+  console.error(
+    `Invalid Stripe publishable key format. ` +
+    `Expected key starting with 'pk_', got: ${STRIPE_KEY.substring(0, 10)}...`
+  );
+}
+
+const stripePromise = STRIPE_KEY ? loadStripe(STRIPE_KEY) : null;
+
+interface StripeCheckoutProps {
+  opened: boolean;
+  onClose: () => void;
+  planGroup: PlanTierGroup;
+  minimumSeats?: number;
+  onSuccess?: (sessionId: string) => void;
+  onError?: (error: string) => void;
+  onLicenseActivated?: (licenseInfo: {licenseType: string; enabled: boolean; maxUsers: number; hasKey: boolean}) => void;
+  hostedCheckoutSuccess?: {
+    isUpgrade: boolean;
+    licenseKey?: string;
+  } | null;
+}
+
+type CheckoutState = {
+  status: 'idle' | 'loading' | 'ready' | 'success' | 'error';
+  clientSecret?: string;
+  error?: string;
+  sessionId?: string;
+};
+
+const StripeCheckout: React.FC<StripeCheckoutProps> = ({
+  opened,
+  onClose,
+  planGroup,
+  minimumSeats = 1,
+  onSuccess,
+  onError,
+  onLicenseActivated,
+  hostedCheckoutSuccess,
+}) => {
+  const { t } = useTranslation();
+  const [state, setState] = useState<CheckoutState>({ status: 'idle' });
+  // Default to yearly if available (better value), otherwise monthly
+  const [selectedPeriod, setSelectedPeriod] = useState<'monthly' | 'yearly'>(
+    planGroup.yearly ? 'yearly' : 'monthly'
+  );
+  const [installationId, setInstallationId] = useState<string | null>(null);
+  const [currentLicenseKey, setCurrentLicenseKey] = useState<string | null>(null);
+  const [licenseKey, setLicenseKey] = useState<string | null>(null);
+  const [pollingStatus, setPollingStatus] = useState<'idle' | 'polling' | 'ready' | 'timeout'>('idle');
+
+  // Refs for polling cleanup
+  const isMountedRef = React.useRef(true);
+  const pollingTimeoutRef = React.useRef<NodeJS.Timeout | null>(null);
+
+  // Get the selected plan based on period
+  const selectedPlan = selectedPeriod === 'yearly' ? planGroup.yearly : planGroup.monthly;
+
+  const createCheckoutSession = async () => {
+    if (!selectedPlan) {
+      setState({
+        status: 'error',
+        error: 'Selected plan period is not available',
+      });
+      return;
+    }
+
+    try {
+      setState({ status: 'loading' });
+
+      // Fetch installation ID from backend
+      let fetchedInstallationId = installationId;
+      if (!fetchedInstallationId) {
+        fetchedInstallationId = await licenseService.getInstallationId();
+        setInstallationId(fetchedInstallationId);
+      }
+
+      // Fetch current license key for upgrades
+      let existingLicenseKey: string | undefined;
+      try {
+        const licenseInfo = await licenseService.getLicenseInfo();
+        if (licenseInfo && licenseInfo.licenseKey) {
+          existingLicenseKey = licenseInfo.licenseKey;
+          setCurrentLicenseKey(existingLicenseKey);
+          console.log('Found existing license for upgrade');
+        }
+      } catch (error) {
+        console.warn('Could not fetch license info, proceeding as new license:', error);
+      }
+
+      const response = await licenseService.createCheckoutSession({
+        lookup_key: selectedPlan.lookupKey,
+        installation_id: fetchedInstallationId,
+        current_license_key: existingLicenseKey,
+        requires_seats: selectedPlan.requiresSeats,
+        seat_count: Math.max(1, Math.min(minimumSeats || 1, 10000)),
+      });
+
+      // Check if we got a redirect URL (hosted checkout for HTTP)
+      if (response.url) {
+        console.log('Redirecting to Stripe hosted checkout:', response.url);
+        // Redirect to Stripe's hosted checkout page
+        window.location.href = response.url;
+        return;
+      }
+
+      // Otherwise, use embedded checkout (HTTPS)
+      setState({
+        status: 'ready',
+        clientSecret: response.clientSecret,
+        sessionId: response.sessionId,
+      });
+    } catch (err) {
+      const errorMessage =
+        err instanceof Error ? err.message : 'Failed to create checkout session';
+      setState({
+        status: 'error',
+        error: errorMessage,
+      });
+      onError?.(errorMessage);
+    }
+  };
+
+  const pollForLicenseKey = useCallback(async (installId: string) => {
+    // Use shared polling utility
+    const result = await pollLicenseKeyWithBackoff(installId, {
+      isMounted: () => isMountedRef.current,
+      onStatusChange: setPollingStatus,
+    });
+
+    if (result.success && result.licenseKey) {
+      setLicenseKey(result.licenseKey);
+
+      // Activate the license key
+      const activation = await activateLicenseKey(result.licenseKey, {
+        isMounted: () => isMountedRef.current,
+        onActivated: onLicenseActivated,
+      });
+
+      if (!activation.success) {
+        console.error('Failed to activate license key:', activation.error);
+      }
+    } else if (result.timedOut) {
+      console.warn('License key polling timed out');
+    } else if (result.error) {
+      console.error('License key polling failed:', result.error);
+    }
+  }, [onLicenseActivated]);
+
+  const handlePaymentComplete = async () => {
+    // Preserve state when changing status
+    setState(prev => ({ ...prev, status: 'success' }));
+
+    // Check if this is an upgrade (existing license key) or new plan
+    if (currentLicenseKey) {
+      // UPGRADE FLOW: Resync existing license with Keygen
+      console.log('Upgrade detected - resyncing existing license with Keygen');
+      setPollingStatus('polling');
+
+      const activation = await resyncExistingLicense({
+        isMounted: () => true, // Modal is open, no need to check
+        onActivated: onLicenseActivated,
+      });
+
+      if (activation.success) {
+        console.log(`License upgraded successfully: ${activation.licenseType}`);
+        setPollingStatus('ready');
+      } else {
+        console.error('Failed to sync upgraded license:', activation.error);
+        setPollingStatus('timeout');
+      }
+
+      // Notify parent (don't wait - upgrade is complete)
+      onSuccess?.(state.sessionId || '');
+    } else {
+      // NEW PLAN FLOW: Poll for new license key
+      console.log('New subscription - polling for license key');
+
+      if (installationId) {
+        pollForLicenseKey(installationId).finally(() => {
+          // Only notify parent after polling completes or times out
+          onSuccess?.(state.sessionId || '');
+        });
+      } else {
+        // No installation ID, notify immediately
+        onSuccess?.(state.sessionId || '');
+      }
+    }
+  };
+
+  const handleClose = () => {
+    // Clear any active polling
+    if (pollingTimeoutRef.current) {
+      clearTimeout(pollingTimeoutRef.current);
+      pollingTimeoutRef.current = null;
+    }
+
+    setState({ status: 'idle' });
+    setPollingStatus('idle');
+    setCurrentLicenseKey(null);
+    setLicenseKey(null);
+    // Reset to default period on close
+    setSelectedPeriod(planGroup.yearly ? 'yearly' : 'monthly');
+    onClose();
+  };
+
+  const handlePeriodChange = (value: string) => {
+    setSelectedPeriod(value as 'monthly' | 'yearly');
+    // Reset state to trigger checkout reload
+    setState({ status: 'idle' });
+  };
+
+  // Cleanup on unmount
+  useEffect(() => {
+    isMountedRef.current = true;
+
+    return () => {
+      isMountedRef.current = false;
+      if (pollingTimeoutRef.current) {
+        clearTimeout(pollingTimeoutRef.current);
+        pollingTimeoutRef.current = null;
+      }
+    };
+  }, []);
+
+  // Handle hosted checkout success - open directly to success state
+  useEffect(() => {
+    if (opened && hostedCheckoutSuccess) {
+      console.log('Opening modal to success state for hosted checkout return');
+
+      // Set appropriate state based on upgrade vs new subscription
+      if (hostedCheckoutSuccess.isUpgrade) {
+        setCurrentLicenseKey('existing'); // Flag to indicate upgrade
+        setPollingStatus('ready');
+      } else if (hostedCheckoutSuccess.licenseKey) {
+        setLicenseKey(hostedCheckoutSuccess.licenseKey);
+        setPollingStatus('ready');
+      }
+
+      // Set to success state to show success UI
+      setState({ status: 'success' });
+    }
+  }, [opened, hostedCheckoutSuccess]);
+
+  // Initialize checkout when modal opens or period changes
+  useEffect(() => {
+    // Don't reset if we're showing success state (license key)
+    if (state.status === 'success') {
+      return;
+    }
+
+    // Skip initialization if opening for hosted checkout success
+    if (hostedCheckoutSuccess) {
+      return;
+    }
+
+    if (opened && state.status === 'idle') {
+      createCheckoutSession();
+    } else if (!opened) {
+      setState({ status: 'idle' });
+    }
+  }, [opened, selectedPeriod, state.status, hostedCheckoutSuccess]);
+
+  const renderContent = () => {
+    // Check if Stripe is configured
+    if (!stripePromise) {
+      return (
+        <Alert color="red" title={t('payment.stripeNotConfigured', 'Stripe Not Configured')}>
+          <Stack gap="md">
+            <Text size="sm">
+              {t(
+                'payment.stripeNotConfiguredMessage',
+                'Stripe payment integration is not configured. Please contact your administrator.'
+              )}
+            </Text>
+            <Button variant="outline" onClick={handleClose}>
+              {t('common.close', 'Close')}
+            </Button>
+          </Stack>
+        </Alert>
+      );
+    }
+
+    switch (state.status) {
+      case 'loading':
+        return (
+          <Stack align="center" justify="center" style={{ padding: '2rem 0' }}>
+            <Loader size="lg" />
+            <Text size="sm" c="dimmed" mt="md">
+              {t('payment.preparing', 'Preparing your checkout...')}
+            </Text>
+          </Stack>
+        );
+
+      case 'ready':
+        {
+        if (!state.clientSecret || !selectedPlan) return null;
+
+        // Build period selector data with prices
+        const periodData = [];
+        if (planGroup.monthly) {
+          const monthlyPrice = planGroup.monthly.requiresSeats && planGroup.monthly.seatPrice
+            ? `${planGroup.monthly.currency}${planGroup.monthly.price.toFixed(2)}${planGroup.monthly.period} + ${planGroup.monthly.currency}${planGroup.monthly.seatPrice.toFixed(2)}/seat`
+            : `${planGroup.monthly.currency}${planGroup.monthly.price.toFixed(2)}${planGroup.monthly.period}`;
+
+          periodData.push({
+            value: 'monthly',
+            label: `${t('payment.monthly', 'Monthly')} - ${monthlyPrice}`,
+          });
+        }
+        if (planGroup.yearly) {
+          const yearlyPrice = planGroup.yearly.requiresSeats && planGroup.yearly.seatPrice
+            ? `${planGroup.yearly.currency}${planGroup.yearly.price.toFixed(2)}${planGroup.yearly.period} + ${planGroup.yearly.currency}${planGroup.yearly.seatPrice.toFixed(2)}/seat`
+            : `${planGroup.yearly.currency}${planGroup.yearly.price.toFixed(2)}${planGroup.yearly.period}`;
+
+          periodData.push({
+            value: 'yearly',
+            label: `${t('payment.yearly', 'Yearly')} - ${yearlyPrice}`,
+          });
+        }
+
+        return (
+          <Grid gutter="md">
+            {/* Left: Period Selector - only show if both periods available */}
+            {periodData.length > 1 && (
+              <Grid.Col span={3}>
+                <Stack gap="sm" style={{ height: '100%' }}>
+                  <Text size="sm" fw={600}>
+                    {t('payment.billingPeriod', 'Billing Period')}
+                  </Text>
+                  <SegmentedControl
+                    value={selectedPeriod}
+                    onChange={handlePeriodChange}
+                    data={periodData}
+                    orientation="vertical"
+                    fullWidth
+                  />
+                  {selectedPlan.requiresSeats && selectedPlan.seatPrice && (
+                    <Text size="xs" c="dimmed" mt="md">
+                      {t('payment.enterpriseNote', 'Seats can be adjusted in checkout (1-1000).')}
+                    </Text>
+                  )}
+                </Stack>
+              </Grid.Col>
+            )}
+
+            {/* Right: Stripe Checkout */}
+            <Grid.Col span={periodData.length > 1 ? 9 : 12}>
+              <EmbeddedCheckoutProvider
+                key={state.clientSecret}
+                stripe={stripePromise}
+                options={{
+                  clientSecret: state.clientSecret,
+                  onComplete: handlePaymentComplete,
+                }}
+              >
+                <EmbeddedCheckout />
+              </EmbeddedCheckoutProvider>
+            </Grid.Col>
+          </Grid>
+        );
+      }
+      case 'success':
+        return (
+          <Alert color="green" title={t('payment.success', 'Payment Successful!')}>
+            <Stack gap="md">
+              <Text size="sm">
+                {t(
+                  'payment.successMessage',
+                  'Your subscription has been activated successfully.'
+                )}
+              </Text>
+
+              {/* License Key Polling Status */}
+              {pollingStatus === 'polling' && (
+                <Group gap="xs">
+                  <Loader size="sm" />
+                  <Text size="sm" c="dimmed">
+                    {currentLicenseKey
+                      ? t('payment.syncingLicense', 'Syncing your upgraded license...')
+                      : t('payment.generatingLicense', 'Generating your license key...')}
+                  </Text>
+                </Group>
+              )}
+
+              {pollingStatus === 'ready' && !currentLicenseKey && licenseKey && (
+                <Paper withBorder p="md" radius="md" bg="gray.1">
+                  <Stack gap="sm">
+                    <Text size="sm" fw={600}>
+                      {t('payment.licenseKey', 'Your License Key')}
+                    </Text>
+                    <Code block>{licenseKey}</Code>
+                    <Button
+                      variant="light"
+                      size="sm"
+                      onClick={() => navigator.clipboard.writeText(licenseKey)}
+                    >
+                      {t('common.copy', 'Copy to Clipboard')}
+                    </Button>
+                    <Text size="xs" c="dimmed">
+                      {t(
+                        'payment.licenseInstructions',
+                        'Enter this key in Settings → Admin Plan → License Key section'
+                      )}
+                    </Text>
+                  </Stack>
+                </Paper>
+              )}
+
+              {pollingStatus === 'ready' && currentLicenseKey && (
+                <Alert color="green" title={t('payment.upgradeComplete', 'Upgrade Complete')}>
+                  <Text size="sm">
+                    {t(
+                      'payment.upgradeCompleteMessage',
+                      'Your subscription has been upgraded successfully. Your existing license key has been updated.'
+                    )}
+                  </Text>
+                </Alert>
+              )}
+
+              {pollingStatus === 'timeout' && (
+                <Alert color="yellow" title={t('payment.licenseDelayed', 'License Key Processing')}>
+                  <Text size="sm">
+                    {t(
+                      'payment.licenseDelayedMessage',
+                      'Your license key is being generated. Please check your email shortly or contact support.'
+                    )}
+                  </Text>
+                </Alert>
+              )}
+
+              {pollingStatus === 'ready' && (
+                <Text size="xs" c="dimmed">
+                  {t('payment.canCloseWindow', 'You can now close this window.')}
+                </Text>
+              )}
+            </Stack>
+          </Alert>
+        );
+
+      case 'error':
+        return (
+          <Alert color="red" title={t('payment.error', 'Payment Error')}>
+            <Stack gap="md">
+              <Text size="sm">{state.error}</Text>
+              <Button variant="outline" onClick={handleClose}>
+                {t('common.close', 'Close')}
+              </Button>
+            </Stack>
+          </Alert>
+        );
+
+      default:
+        return null;
+    }
+  };
+
+  return (
+    <Modal
+      opened={opened}
+      onClose={handleClose}
+      title={
+        <Text fw={600} size="lg">
+          {t('payment.upgradeTitle', 'Upgrade to {{planName}}', { planName: planGroup.name })}
+        </Text>
+      }
+      size="90%"
+      centered
+      withCloseButton={true}
+      closeOnEscape={true}
+      closeOnClickOutside={false}
+      zIndex={Z_INDEX_OVER_CONFIG_MODAL}
+      styles={{
+        body: {
+          minHeight: '85vh',
+        },
+        content: {
+          maxHeight: '95vh',
+        },
+      }}
+    >
+      {renderContent()}
+    </Modal>
+  );
+};
+
+export default StripeCheckout;
diff --git a/frontend/src/proprietary/components/shared/UpgradeBanner.tsx b/frontend/src/proprietary/components/shared/UpgradeBanner.tsx
new file mode 100644
index 000000000..93a5eb827
--- /dev/null
+++ b/frontend/src/proprietary/components/shared/UpgradeBanner.tsx
@@ -0,0 +1,144 @@
+import React, { useState, useEffect } from 'react';
+import { Group, Text, Button, ActionIcon, Paper } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import { useAuth } from '@app/auth/UseSession';
+import { useCheckout } from '@app/contexts/CheckoutContext';
+import { useLicense } from '@app/contexts/LicenseContext';
+import { mapLicenseToTier } from '@app/services/licenseService';
+import LocalIcon from '@app/components/shared/LocalIcon';
+import { isSupabaseConfigured } from '@app/services/supabaseClient';
+
+/**
+ * UpgradeBanner - Dismissable top banner encouraging users to upgrade
+ *
+ * This component demonstrates:
+ * - How to check authentication status with useAuth()
+ * - How to check license status with licenseService
+ * - How to open checkout modal with useCheckout()
+ * - How to persist dismissal state with localStorage
+ *
+ * To remove this banner:
+ * 1. Remove the import and component from AppProviders.tsx
+ * 2. Delete this file
+ */
+const UpgradeBanner: React.FC = () => {
+  const { t } = useTranslation();
+  const { user } = useAuth();
+  const { openCheckout } = useCheckout();
+  const { licenseInfo, loading: licenseLoading } = useLicense();
+  const [isVisible, setIsVisible] = useState(false);
+
+  // Check if user should see the banner
+  useEffect(() => {
+    // Don't show if not logged in
+    if (!user) {
+      setIsVisible(false);
+      return;
+    }
+
+    // Don't show if Supabase is not configured (no checkout available)
+    if (!isSupabaseConfigured) {
+      setIsVisible(false);
+      return;
+    }
+
+    // Don't show while license is loading
+    if (licenseLoading) {
+      return;
+    }
+
+    // Check if banner was dismissed
+    const dismissed = localStorage.getItem('upgradeBannerDismissed');
+    if (dismissed === 'true') {
+      setIsVisible(false);
+      return;
+    }
+
+    // Check license status from global context
+    const tier = mapLicenseToTier(licenseInfo);
+
+    // Show banner only for free tier users
+    if (tier === 'free' || tier === null) {
+      setIsVisible(true);
+    } else {
+      // Auto-hide banner if user upgrades
+      setIsVisible(false);
+    }
+  }, [user, licenseInfo, licenseLoading]);
+
+  // Handle dismiss
+  const handleDismiss = () => {
+    localStorage.setItem('upgradeBannerDismissed', 'true');
+    setIsVisible(false);
+  };
+
+  // Handle upgrade button click
+  const handleUpgrade = () => {
+    openCheckout('server', {
+      currency: 'gbp',
+      minimumSeats: 1,
+      onSuccess: () => {
+        // Banner will auto-hide on next render when license is detected
+        setIsVisible(false);
+      },
+    });
+  };
+
+  // Don't render anything if loading or not visible
+  if (licenseLoading || !isVisible) {
+    return null;
+  }
+
+  return (
+    <Paper
+      shadow="sm"
+      p="md"
+      style={{
+        position: 'fixed',
+        top: 0,
+        left: 0,
+        right: 0,
+        zIndex: 1000,
+        borderRadius: 0,
+        background: 'linear-gradient(135deg, #667eea 0%, #764ba2 100%)',
+        color: 'white',
+      }}
+    >
+      <Group justify="space-between" wrap="nowrap">
+        <Group gap="md" wrap="nowrap">
+          <LocalIcon icon="stars-rounded" width="1.5rem" height="1.5rem" />
+          <div>
+            <Text size="sm" fw={600}>
+              {t('upgradeBanner.title', 'Upgrade to Server Plan')}
+            </Text>
+            <Text size="xs" opacity={0.9}>
+              {t('upgradeBanner.message', 'Get the most out of Stirling PDF with unlimited users and advanced features')}
+            </Text>
+          </div>
+        </Group>
+
+        <Group gap="xs" wrap="nowrap">
+          <Button
+            variant="white"
+            size="sm"
+            onClick={handleUpgrade}
+            leftSection={<LocalIcon icon="upgrade-rounded" width="1rem" height="1rem" />}
+          >
+            {t('upgradeBanner.upgradeButton', 'Upgrade Now')}
+          </Button>
+          <ActionIcon
+            variant="subtle"
+            color="white"
+            size="lg"
+            onClick={handleDismiss}
+            aria-label={t('upgradeBanner.dismiss', 'Dismiss banner')}
+          >
+            <LocalIcon icon="close-rounded" width="1.25rem" height="1.25rem" />
+          </ActionIcon>
+        </Group>
+      </Group>
+    </Paper>
+  );
+};
+
+export default UpgradeBanner;
diff --git a/frontend/src/proprietary/components/shared/config/configNavSections.tsx b/frontend/src/proprietary/components/shared/config/configNavSections.tsx
index bc63e979a..2b27a4ba9 100644
--- a/frontend/src/proprietary/components/shared/config/configNavSections.tsx
+++ b/frontend/src/proprietary/components/shared/config/configNavSections.tsx
@@ -10,6 +10,7 @@ import AdminDatabaseSection from '@app/components/shared/config/configSections/A
 import AdminAdvancedSection from '@app/components/shared/config/configSections/AdminAdvancedSection';
 import AdminLegalSection from '@app/components/shared/config/configSections/AdminLegalSection';
 import AdminPremiumSection from '@app/components/shared/config/configSections/AdminPremiumSection';
+import AdminPlanSection from '@app/components/shared/config/configSections/AdminPlanSection';
 import AdminFeaturesSection from '@app/components/shared/config/configSections/AdminFeaturesSection';
 import AdminEndpointsSection from '@app/components/shared/config/configSections/AdminEndpointsSection';
 import AdminAuditSection from '@app/components/shared/config/configSections/AdminAuditSection';
@@ -136,6 +137,14 @@ export const createConfigNavSections = (
           disabled: requiresLogin,
           disabledTooltip: requiresLogin ? 'Enable login mode first' : undefined
         },
+        {
+          key: 'adminPlan',
+          label: 'Plan',
+          icon: 'star-rounded',
+          component: <AdminPlanSection />,
+          disabled: requiresLogin,
+          disabledTooltip: requiresLogin ? 'Enable login mode first' : undefined
+        },
         {
           key: 'adminAudit',
           label: 'Audit',
diff --git a/frontend/src/proprietary/components/shared/config/configSections/AdminPlanSection.tsx b/frontend/src/proprietary/components/shared/config/configSections/AdminPlanSection.tsx
new file mode 100644
index 000000000..522658004
--- /dev/null
+++ b/frontend/src/proprietary/components/shared/config/configSections/AdminPlanSection.tsx
@@ -0,0 +1,240 @@
+import React, { useState, useCallback, useEffect } from 'react';
+import { Divider, Loader, Alert, Select, Group, Text, Collapse, Button, TextInput, Stack, Paper } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import { usePlans } from '@app/hooks/usePlans';
+import licenseService, { PlanTierGroup } from '@app/services/licenseService';
+import { useCheckout } from '@app/contexts/CheckoutContext';
+import { useLicense } from '@app/contexts/LicenseContext';
+import AvailablePlansSection from '@app/components/shared/config/configSections/plan/AvailablePlansSection';
+import StaticPlanSection from '@app/components/shared/config/configSections/plan/StaticPlanSection';
+import { alert } from '@app/components/toast';
+import LocalIcon from '@app/components/shared/LocalIcon';
+import { Z_INDEX_OVER_CONFIG_MODAL } from '@app/styles/zIndex';
+import { ManageBillingButton } from '@app/components/shared/ManageBillingButton';
+import { isSupabaseConfigured } from '@app/services/supabaseClient';
+
+const AdminPlanSection: React.FC = () => {
+  const { t } = useTranslation();
+  const { openCheckout } = useCheckout();
+  const { licenseInfo, refetchLicense } = useLicense();
+  const [currency, setCurrency] = useState<string>('gbp');
+  const [useStaticVersion, setUseStaticVersion] = useState(false);
+  const [showLicenseKey, setShowLicenseKey] = useState(false);
+  const [licenseKeyInput, setLicenseKeyInput] = useState<string>('');
+  const [savingLicense, setSavingLicense] = useState(false);
+  const { plans, loading, error, refetch } = usePlans(currency);
+
+  // Check if we should use static version
+  useEffect(() => {
+    // Check if Stripe and Supabase are configured
+    const stripeKey = import.meta.env.VITE_STRIPE_PUBLISHABLE_KEY;
+    if (!stripeKey || !isSupabaseConfigured || error) {
+      setUseStaticVersion(true);
+    }
+  }, [error]);
+
+  const handleSaveLicense = async () => {
+    try {
+      setSavingLicense(true);
+      // Allow empty string to clear/remove license
+      const response = await licenseService.saveLicenseKey(licenseKeyInput.trim());
+
+      if (response.success) {
+        // Refresh license context to update all components
+        await refetchLicense();
+
+        alert({
+          alertType: 'success',
+          title: t('admin.settings.premium.key.success', 'License Key Saved'),
+          body: t('admin.settings.premium.key.successMessage', 'Your license key has been activated successfully. No restart required.'),
+        });
+
+        // Clear input
+        setLicenseKeyInput('');
+      } else {
+        alert({
+          alertType: 'error',
+          title: t('admin.error', 'Error'),
+          body: response.error || t('admin.settings.saveError', 'Failed to save license key'),
+        });
+      }
+    } catch (error) {
+      console.error('Failed to save license key:', error);
+      alert({
+        alertType: 'error',
+        title: t('admin.error', 'Error'),
+        body: t('admin.settings.saveError', 'Failed to save license key'),
+      });
+    } finally {
+      setSavingLicense(false);
+    }
+  };
+
+  const currencyOptions = [
+    { value: 'gbp', label: 'British pound (GBP, £)' },
+    { value: 'usd', label: 'US dollar (USD, $)' },
+    { value: 'eur', label: 'Euro (EUR, €)' },
+    { value: 'cny', label: 'Chinese yuan (CNY, ¥)' },
+    { value: 'inr', label: 'Indian rupee (INR, ₹)' },
+    { value: 'brl', label: 'Brazilian real (BRL, R$)' },
+    { value: 'idr', label: 'Indonesian rupiah (IDR, Rp)' },
+  ];
+
+  const handleUpgradeClick = useCallback(
+    (planGroup: PlanTierGroup) => {
+      // Only allow upgrades for server and enterprise tiers
+      if (planGroup.tier === 'free') {
+        return;
+      }
+
+      // Use checkout context to open checkout modal
+      openCheckout(planGroup.tier, {
+        currency,
+        onSuccess: () => {
+          // Refetch plans after successful payment
+          // License context will auto-update
+          refetch();
+        },
+      });
+    },
+    [openCheckout, currency, refetch]
+  );
+
+  // Show static version if Stripe is not configured or there's an error
+  if (useStaticVersion) {
+    return <StaticPlanSection currentLicenseInfo={licenseInfo ?? undefined} />;
+  }
+
+  // Early returns after all hooks are called
+  if (loading) {
+    return (
+      <div style={{ display: 'flex', justifyContent: 'center', alignItems: 'center', padding: '2rem 0' }}>
+        <Loader size="lg" />
+      </div>
+    );
+  }
+
+  if (error) {
+    // Fallback to static version on error
+    return <StaticPlanSection currentLicenseInfo={licenseInfo ?? undefined} />;
+  }
+
+  if (!plans || plans.length === 0) {
+    return (
+      <Alert color="yellow" title="No data available">
+        Plans data is not available at the moment.
+      </Alert>
+    );
+  }
+
+  return (
+    <div style={{ display: 'flex', flexDirection: 'column', gap: '2rem' }}>
+      {/* Currency Selection & Manage Subscription */}
+      <Paper withBorder p="md" radius="md">
+        <Stack gap="md">
+          <Group justify="space-between" align="center">
+            <Text size="lg" fw={600}>
+              {t('plan.currency', 'Currency')}
+            </Text>
+            <Select
+              value={currency}
+              onChange={(value) => setCurrency(value || 'gbp')}
+              data={currencyOptions}
+              searchable
+              clearable={false}
+              w={300}
+              comboboxProps={{ withinPortal: true, zIndex: Z_INDEX_OVER_CONFIG_MODAL }}
+            />
+          </Group>
+
+          {/* Manage Subscription Button - Only show if user has active license and Supabase is configured */}
+          {licenseInfo?.licenseKey && isSupabaseConfigured && (
+            <Group justify="space-between" align="center">
+              <Text size="sm" c="dimmed">
+                {t('plan.manageSubscription.description', 'Manage your subscription, billing, and payment methods')}
+              </Text>
+              <ManageBillingButton />
+            </Group>
+          )}
+        </Stack>
+      </Paper>
+
+      <AvailablePlansSection
+        plans={plans}
+        currentLicenseInfo={licenseInfo}
+        onUpgradeClick={handleUpgradeClick}
+      />
+
+      <Divider />
+
+      {/* License Key Section */}
+      <div>
+        <Button
+          variant="subtle"
+          leftSection={<LocalIcon icon={showLicenseKey ? "expand-less-rounded" : "expand-more-rounded"} width="1.25rem" height="1.25rem" />}
+          onClick={() => setShowLicenseKey(!showLicenseKey)}
+        >
+          {t('admin.settings.premium.licenseKey.toggle', 'Got a license key or certificate file?')}
+        </Button>
+
+        <Collapse in={showLicenseKey} mt="md">
+          <Stack gap="md">
+            <Alert
+              variant="light"
+              color="blue"
+              icon={<LocalIcon icon="info-rounded" width="1rem" height="1rem" />}
+            >
+              <Text size="sm">
+                {t('admin.settings.premium.licenseKey.info', 'If you have a license key or certificate file from a direct purchase, you can enter it here to activate premium or enterprise features.')}
+              </Text>
+            </Alert>
+
+            {/* Severe warning if license already exists */}
+            {licenseInfo?.licenseKey && (
+              <Alert
+                variant="light"
+                color="red"
+                icon={<LocalIcon icon="warning-rounded" width="1rem" height="1rem" />}
+                title={t('admin.settings.premium.key.overwriteWarning.title', '⚠️ Warning: Existing License Detected')}
+              >
+                <Stack gap="xs">
+                  <Text size="sm" fw={600}>
+                    {t('admin.settings.premium.key.overwriteWarning.line1', 'Overwriting your current license key cannot be undone.')}
+                  </Text>
+                  <Text size="sm">
+                    {t('admin.settings.premium.key.overwriteWarning.line2', 'Your previous license will be permanently lost unless you have backed it up elsewhere.')}
+                  </Text>
+                  <Text size="sm" fw={500}>
+                    {t('admin.settings.premium.key.overwriteWarning.line3', 'Important: Keep license keys private and secure. Never share them publicly.')}
+                  </Text>
+                </Stack>
+              </Alert>
+            )}
+
+            <Paper withBorder p="md" radius="md">
+              <Stack gap="md">
+                <TextInput
+                  label={t('admin.settings.premium.key.label', 'License Key')}
+                  description={t('admin.settings.premium.key.description', 'Enter your premium or enterprise license key. Premium features will be automatically enabled when a key is provided.')}
+                  value={licenseKeyInput}
+                  onChange={(e) => setLicenseKeyInput(e.target.value)}
+                  placeholder={licenseInfo?.licenseKey || '00000000-0000-0000-0000-000000000000'}
+                  type="password"
+                  disabled={savingLicense}
+                />
+
+                <Group justify="flex-end">
+                  <Button onClick={handleSaveLicense} loading={savingLicense} size="sm">
+                    {t('admin.settings.save', 'Save Changes')}
+                  </Button>
+                </Group>
+              </Stack>
+            </Paper>
+          </Stack>
+        </Collapse>
+      </div>
+    </div>
+  );
+};
+
+export default AdminPlanSection;
diff --git a/frontend/src/proprietary/components/shared/config/configSections/plan/AvailablePlansSection.tsx b/frontend/src/proprietary/components/shared/config/configSections/plan/AvailablePlansSection.tsx
new file mode 100644
index 000000000..2c0640a3f
--- /dev/null
+++ b/frontend/src/proprietary/components/shared/config/configSections/plan/AvailablePlansSection.tsx
@@ -0,0 +1,109 @@
+import React, { useState, useMemo } from 'react';
+import { Button, Collapse } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import licenseService, { PlanTier, PlanTierGroup, LicenseInfo, mapLicenseToTier } from '@app/services/licenseService';
+import PlanCard from '@app/components/shared/config/configSections/plan/PlanCard';
+import FeatureComparisonTable from '@app/components/shared/config/configSections/plan/FeatureComparisonTable';
+
+interface AvailablePlansSectionProps {
+  plans: PlanTier[];
+  currentPlanId?: string;
+  currentLicenseInfo?: LicenseInfo | null;
+  onUpgradeClick: (planGroup: PlanTierGroup) => void;
+}
+
+const AvailablePlansSection: React.FC<AvailablePlansSectionProps> = ({
+  plans,
+  currentLicenseInfo,
+  onUpgradeClick,
+}) => {
+  const { t } = useTranslation();
+  const [showComparison, setShowComparison] = useState(false);
+
+  // Group plans by tier (Free, Server, Enterprise)
+  const groupedPlans = useMemo(() => {
+    return licenseService.groupPlansByTier(plans);
+  }, [plans]);
+
+  // Calculate current tier from license info
+  const currentTier = useMemo(() => {
+    return mapLicenseToTier(currentLicenseInfo || null);
+  }, [currentLicenseInfo]);
+
+  // Determine if the current tier matches (checks both Stripe subscription and license)
+  const isCurrentTier = (tierGroup: PlanTierGroup): boolean => {
+    // Check license tier match
+    if (currentTier && tierGroup.tier === currentTier) {
+      return true;
+    }
+    return false;
+  };
+
+  // Determine if selecting this plan would be a downgrade
+  const isDowngrade = (tierGroup: PlanTierGroup): boolean => {
+    if (!currentTier) return false;
+
+    // Define tier hierarchy: enterprise > server > free
+    const tierHierarchy: Record<string, number> = {
+      'enterprise': 3,
+      'server': 2,
+      'free': 1
+    };
+
+    const currentLevel = tierHierarchy[currentTier] || 0;
+    const targetLevel = tierHierarchy[tierGroup.tier] || 0;
+
+    return currentLevel > targetLevel;
+  };
+
+  return (
+    <div>
+      <h3 style={{ margin: 0, color: 'var(--mantine-color-text)', fontSize: '1rem' }}>
+        {t('plan.availablePlans.title', 'Available Plans')}
+      </h3>
+      <p
+        style={{
+          margin: '0.25rem 0 1rem 0',
+          color: 'var(--mantine-color-dimmed)',
+          fontSize: '0.875rem',
+        }}
+      >
+        {t('plan.availablePlans.subtitle', 'Choose the plan that fits your needs')}
+      </p>
+
+      <div
+        style={{
+          display: 'grid',
+          gridTemplateColumns: 'repeat(3, 1fr)',
+          gap: '1rem',
+          marginBottom: '1rem',
+        }}
+      >
+        {groupedPlans.map((group) => (
+          <PlanCard
+            key={group.tier}
+            planGroup={group}
+            isCurrentTier={isCurrentTier(group)}
+            isDowngrade={isDowngrade(group)}
+            currentLicenseInfo={currentLicenseInfo}
+            onUpgradeClick={onUpgradeClick}
+          />
+        ))}
+      </div>
+
+      <div style={{ textAlign: 'center' }}>
+        <Button variant="subtle" onClick={() => setShowComparison(!showComparison)}>
+          {showComparison
+            ? t('plan.hideComparison', 'Hide Feature Comparison')
+            : t('plan.showComparison', 'Compare All Features')}
+        </Button>
+      </div>
+
+      <Collapse in={showComparison}>
+        <FeatureComparisonTable plans={groupedPlans} />
+      </Collapse>
+    </div>
+  );
+};
+
+export default AvailablePlansSection;
diff --git a/frontend/src/proprietary/components/shared/config/configSections/plan/FeatureComparisonTable.tsx b/frontend/src/proprietary/components/shared/config/configSections/plan/FeatureComparisonTable.tsx
new file mode 100644
index 000000000..129d59b9f
--- /dev/null
+++ b/frontend/src/proprietary/components/shared/config/configSections/plan/FeatureComparisonTable.tsx
@@ -0,0 +1,93 @@
+import React from 'react';
+import { Card, Badge, Text } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import { PlanFeature } from '@app/services/licenseService';
+
+interface PlanWithFeatures {
+  name: string;
+  features: PlanFeature[];
+  popular?: boolean;
+  tier?: string;
+}
+
+interface FeatureComparisonTableProps {
+  plans: PlanWithFeatures[];
+}
+
+const FeatureComparisonTable: React.FC<FeatureComparisonTableProps> = ({ plans }) => {
+  const { t } = useTranslation();
+
+  return (
+    <Card padding="lg" radius="md" withBorder style={{ marginTop: '1rem' }}>
+      <Text size="lg" fw={600} mb="md">
+        {t('plan.featureComparison', 'Feature Comparison')}
+      </Text>
+
+      <div style={{ overflowX: 'auto' }}>
+        <table style={{ width: '100%', borderCollapse: 'collapse' }}>
+          <thead>
+            <tr style={{ borderBottom: '2px solid var(--mantine-color-gray-3)' }}>
+              <th style={{ textAlign: 'left', padding: '0.75rem' }}>
+                {t('plan.feature.title', 'Feature')}
+              </th>
+              {plans.map((plan, index) => (
+                <th
+                  key={plan.tier || plan.name || index}
+                  style={{
+                    textAlign: 'center',
+                    padding: '0.75rem',
+                    minWidth: '8rem',
+                    position: 'relative'
+                  }}
+                >
+                  {plan.name}
+                  {plan.popular && (
+                    <Badge
+                      color="blue"
+                      variant="filled"
+                      size="xs"
+                      style={{
+                        position: 'absolute',
+                        top: '0.5rem',
+                        right: '0.5rem',
+                      }}
+                    >
+                      {t('plan.popular', 'Popular')}
+                    </Badge>
+                  )}
+                </th>
+              ))}
+            </tr>
+          </thead>
+          <tbody>
+            {plans[0]?.features.map((_, featureIndex) => (
+              <tr
+                key={featureIndex}
+                style={{ borderBottom: '1px solid var(--mantine-color-gray-3)' }}
+              >
+                <td style={{ padding: '0.75rem' }}>
+                  {plans[0].features[featureIndex].name}
+                </td>
+                {plans.map((plan, planIndex) => (
+                  <td key={planIndex} style={{ textAlign: 'center', padding: '0.75rem' }}>
+                    {plan.features[featureIndex]?.included ? (
+                      <Text c="green" fw={600} size="lg">
+                        ✓
+                      </Text>
+                    ) : (
+                      <Text c="gray" size="sm">
+                        −
+                      </Text>
+                    )}
+                  </td>
+                ))}
+              </tr>
+            ))}
+          </tbody>
+        </table>
+      </div>
+    </Card>
+  );
+};
+
+export default FeatureComparisonTable;
diff --git a/frontend/src/proprietary/components/shared/config/configSections/plan/PlanCard.tsx b/frontend/src/proprietary/components/shared/config/configSections/plan/PlanCard.tsx
new file mode 100644
index 000000000..696fa50e9
--- /dev/null
+++ b/frontend/src/proprietary/components/shared/config/configSections/plan/PlanCard.tsx
@@ -0,0 +1,202 @@
+import React from 'react';
+import { Button, Card, Badge, Text, Stack, Divider } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import { PlanTierGroup, LicenseInfo } from '@app/services/licenseService';
+
+interface PlanCardProps {
+  planGroup: PlanTierGroup;
+  isCurrentTier: boolean;
+  isDowngrade: boolean;
+  currentLicenseInfo?: LicenseInfo | null;
+  onUpgradeClick: (planGroup: PlanTierGroup) => void;
+}
+
+const PlanCard: React.FC<PlanCardProps> = ({ planGroup, isCurrentTier, isDowngrade, currentLicenseInfo, onUpgradeClick }) => {
+  const { t } = useTranslation();
+
+  // Render Free plan
+  if (planGroup.tier === 'free') {
+    return (
+      <Card
+        padding="lg"
+        radius="md"
+        withBorder
+        style={{
+          position: 'relative',
+          display: 'flex',
+          flexDirection: 'column',
+          minHeight: '400px',
+          borderColor: isCurrentTier ? 'var(--mantine-color-green-6)' : undefined,
+          borderWidth: isCurrentTier ? '2px' : undefined,
+        }}
+      >
+        {isCurrentTier && (
+          <Badge
+            color="green"
+            variant="filled"
+            size="sm"
+            style={{ position: 'absolute', top: '1rem', right: '1rem' }}
+          >
+            {t('plan.current', 'Current Plan')}
+          </Badge>
+        )}
+        <Stack gap="md" style={{ height: '100%' }}>
+          <div>
+            <Text size="xl" fw={700} mb="xs">
+              {planGroup.name}
+            </Text>
+            <Text size="xs" c="dimmed" mb="xs" style={{ opacity: 0 }}>
+              {t('plan.from', 'From')}
+            </Text>
+            <Text size="2.5rem" fw={700} style={{ lineHeight: 1 }}>
+              £0
+            </Text>
+            <Text size="sm" c="dimmed" mt="xs">
+              {t('plan.free.forever', 'Forever free')}
+            </Text>
+          </div>
+
+          <Divider />
+
+          <Stack gap="xs">
+            {planGroup.highlights.map((highlight, index) => (
+              <Text key={index} size="sm" c="dimmed">
+                • {highlight}
+              </Text>
+            ))}
+          </Stack>
+
+          <div style={{ flexGrow: 1 }} />
+
+          <Button variant="filled" disabled fullWidth>
+            {isCurrentTier
+              ? t('plan.current', 'Current Plan')
+              : t('plan.free.included', 'Included')}
+          </Button>
+        </Stack>
+      </Card>
+    );
+  }
+
+  // Render Server or Enterprise plans
+  const { monthly, yearly } = planGroup;
+  const isEnterprise = planGroup.tier === 'enterprise';
+
+  // Calculate "From" pricing - show yearly price divided by 12 for lowest monthly equivalent
+  let displayPrice = monthly?.price || 0;
+  let displaySeatPrice = monthly?.seatPrice;
+  let displayCurrency = monthly?.currency || '£';
+
+  if (yearly) {
+    displayPrice = Math.round(yearly.price / 12);
+    displaySeatPrice = yearly.seatPrice ? Math.round(yearly.seatPrice / 12) : undefined;
+    displayCurrency = yearly.currency;
+  }
+
+  return (
+    <Card
+      padding="lg"
+      radius="md"
+      withBorder
+      style={{
+        position: 'relative',
+        display: 'flex',
+        flexDirection: 'column',
+        minHeight: '400px',
+        borderColor: isCurrentTier ? 'var(--mantine-color-green-6)' : undefined,
+        borderWidth: isCurrentTier ? '2px' : undefined,
+      }}
+    >
+      {isCurrentTier ? (
+        <Badge
+          color="green"
+          variant="filled"
+          size="sm"
+          style={{ position: 'absolute', top: '1rem', right: '1rem' }}
+        >
+          {t('plan.current', 'Current Plan')}
+        </Badge>
+      ) : planGroup.popular ? (
+        <Badge
+          variant="filled"
+          size="sm"
+          style={{ position: 'absolute', top: '1rem', right: '1rem' }}
+        >
+          {t('plan.popular', 'Popular')}
+        </Badge>
+      ) : null}
+
+      <Stack gap="md" style={{ height: '100%' }}>
+        {/* Tier Name */}
+        <div>
+          <Text size="xl" fw={700} mb="xs">
+            {planGroup.name}
+          </Text>
+
+          <Text size="xs" c="dimmed" mb="xs">
+            {t('plan.from', 'From')}
+          </Text>
+
+          {/* Price */}
+          {isEnterprise && displaySeatPrice !== undefined ? (
+            <>
+              <Text size="2.5rem" fw={700} style={{ lineHeight: 1 }}>
+                {displayCurrency}{displayPrice}
+              </Text>
+              <Text size="sm" c="dimmed" mt="xs">
+                + {displayCurrency}{displaySeatPrice}/seat {t('plan.perMonth', '/month')}
+              </Text>
+            </>
+          ) : (
+            <>
+              <Text size="2.5rem" fw={700} style={{ lineHeight: 1 }}>
+                {displayCurrency}{displayPrice}
+              </Text>
+              <Text size="sm" c="dimmed" mt="xs">
+                {t('plan.perMonth', '/month')}
+              </Text>
+            </>
+          )}
+
+          {/* Show seat count for enterprise plans when current */}
+          {isEnterprise && isCurrentTier && currentLicenseInfo && currentLicenseInfo.maxUsers > 0 && (
+            <Text size="sm" c="green" fw={500} mt="xs">
+              {t('plan.licensedSeats', 'Licensed: {{count}} seats', { count: currentLicenseInfo.maxUsers })}
+            </Text>
+          )}
+        </div>
+
+        <Divider />
+
+        {/* Highlights */}
+        <Stack gap="xs">
+          {planGroup.highlights.map((highlight, index) => (
+            <Text key={index} size="sm" c="dimmed">
+              • {highlight}
+            </Text>
+          ))}
+        </Stack>
+
+        <div style={{ flexGrow: 1 }} />
+
+        {/* Single Upgrade Button */}
+        <Button
+          variant={isCurrentTier || isDowngrade ? 'light' : 'filled'}
+          fullWidth
+          onClick={() => onUpgradeClick(planGroup)}
+          disabled={isCurrentTier || isDowngrade}
+        >
+          {isCurrentTier
+            ? t('plan.current', 'Current Plan')
+            : isDowngrade
+              ? t('plan.includedInCurrent', 'Included in Your Plan')
+              : isEnterprise
+                ? t('plan.selectPlan', 'Select Plan')
+                : t('plan.upgrade', 'Upgrade')}
+        </Button>
+      </Stack>
+    </Card>
+  );
+};
+
+export default PlanCard;
diff --git a/frontend/src/proprietary/components/shared/config/configSections/plan/StaticPlanSection.tsx b/frontend/src/proprietary/components/shared/config/configSections/plan/StaticPlanSection.tsx
new file mode 100644
index 000000000..3bdd06baf
--- /dev/null
+++ b/frontend/src/proprietary/components/shared/config/configSections/plan/StaticPlanSection.tsx
@@ -0,0 +1,338 @@
+import React, { useState, useEffect } from 'react';
+import { Card, Text, Group, Stack, Badge, Button, Collapse, Alert, TextInput, Paper, Loader, Divider } from '@mantine/core';
+import { useTranslation } from 'react-i18next';
+import LocalIcon from '@app/components/shared/LocalIcon';
+import RestartConfirmationModal from '@app/components/shared/config/RestartConfirmationModal';
+import { useRestartServer } from '@app/components/shared/config/useRestartServer';
+import { useAdminSettings } from '@app/hooks/useAdminSettings';
+import PendingBadge from '@app/components/shared/config/PendingBadge';
+import { alert } from '@app/components/toast';
+import { LicenseInfo, mapLicenseToTier } from '@app/services/licenseService';
+import { PLAN_FEATURES, PLAN_HIGHLIGHTS } from '@app/constants/planConstants';
+import FeatureComparisonTable from '@app/components/shared/config/configSections/plan/FeatureComparisonTable';
+
+interface PremiumSettingsData {
+  key?: string;
+  enabled?: boolean;
+}
+
+interface StaticPlanSectionProps {
+  currentLicenseInfo?: LicenseInfo;
+}
+
+const StaticPlanSection: React.FC<StaticPlanSectionProps> = ({ currentLicenseInfo }) => {
+  const { t } = useTranslation();
+  const [showLicenseKey, setShowLicenseKey] = useState(false);
+  const [showComparison, setShowComparison] = useState(false);
+
+  // Premium/License key management
+  const { restartModalOpened, showRestartModal, closeRestartModal, restartServer } = useRestartServer();
+  const {
+    settings: premiumSettings,
+    setSettings: setPremiumSettings,
+    loading: premiumLoading,
+    saving: premiumSaving,
+    fetchSettings: fetchPremiumSettings,
+    saveSettings: savePremiumSettings,
+    isFieldPending,
+  } = useAdminSettings<PremiumSettingsData>({
+    sectionName: 'premium',
+  });
+
+  useEffect(() => {
+    fetchPremiumSettings();
+  }, []);
+
+  const handleSaveLicense = async () => {
+    try {
+      await savePremiumSettings();
+      showRestartModal();
+    } catch (_error) {
+      alert({
+        alertType: 'error',
+        title: t('admin.error', 'Error'),
+        body: t('admin.settings.saveError', 'Failed to save settings'),
+      });
+    }
+  };
+
+  const staticPlans = [
+    {
+      id: 'free',
+      name: t('plan.free.name', 'Free'),
+      price: 0,
+      currency: '£',
+      period: '',
+      highlights: PLAN_HIGHLIGHTS.FREE,
+      features: PLAN_FEATURES.FREE,
+      maxUsers: 5,
+    },
+    {
+      id: 'server',
+      name: 'Server',
+      price: 0,
+      currency: '',
+      period: '',
+      popular: false,
+      highlights: PLAN_HIGHLIGHTS.SERVER_MONTHLY,
+      features: PLAN_FEATURES.SERVER,
+      maxUsers: 'Unlimited users',
+    },
+    {
+      id: 'enterprise',
+      name: t('plan.enterprise.name', 'Enterprise'),
+      price: 0,
+      currency: '',
+      period: '',
+      highlights: PLAN_HIGHLIGHTS.ENTERPRISE_MONTHLY,
+      features: PLAN_FEATURES.ENTERPRISE,
+      maxUsers: 'Custom',
+    },
+  ];
+
+  const getCurrentPlan = () => {
+    const tier = mapLicenseToTier(currentLicenseInfo || null);
+    if (tier === 'enterprise') return staticPlans[2];
+    if (tier === 'server') return staticPlans[1];
+    return staticPlans[0]; // free
+  };
+
+  const currentPlan = getCurrentPlan();
+
+  return (
+    <div style={{ display: 'flex', flexDirection: 'column', gap: '2rem' }}>
+      {/* Current Plan Section */}
+      <div>
+        <h3 style={{ margin: 0, color: 'var(--mantine-color-text)', fontSize: '1rem' }}>
+          {t('plan.activePlan.title', 'Active Plan')}
+        </h3>
+        <p
+          style={{
+            margin: '0.25rem 0 1rem 0',
+            color: 'var(--mantine-color-dimmed)',
+            fontSize: '0.875rem',
+          }}
+        >
+          {t('plan.activePlan.subtitle', 'Your current subscription details')}
+        </p>
+
+        <Card padding="lg" radius="md" withBorder>
+          <Group justify="space-between" align="center">
+            <Stack gap="xs">
+              <Group gap="sm">
+                <Text size="lg" fw={600}>
+                  {currentPlan.name}
+                </Text>
+                <Badge color="green" variant="light">
+                  {t('subscription.status.active', 'Active')}
+                </Badge>
+              </Group>
+              {currentLicenseInfo && (
+                <Text size="sm" c="dimmed">
+                  {t('plan.static.maxUsers', 'Max Users')}: {currentLicenseInfo.maxUsers}
+                </Text>
+              )}
+            </Stack>
+            <div style={{ textAlign: 'right' }}>
+              <Text size="xl" fw={700}>
+                {currentPlan.price === 0 ? t('plan.free.name', 'Free') : `${currentPlan.currency}${currentPlan.price}${currentPlan.period}`}
+              </Text>
+            </div>
+          </Group>
+        </Card>
+      </div>
+
+      {/* Available Plans */}
+      <div>
+        <h3 style={{ margin: 0, color: 'var(--mantine-color-text)', fontSize: '1rem' }}>
+          {t('plan.availablePlans.title', 'Available Plans')}
+        </h3>
+        <p
+          style={{
+            margin: '0.25rem 0 1rem 0',
+            color: 'var(--mantine-color-dimmed)',
+            fontSize: '0.875rem',
+          }}
+        >
+          {t('plan.static.contactToUpgrade', 'Contact us to upgrade or customize your plan')}
+        </p>
+
+        <div
+          style={{
+            display: 'grid',
+            gridTemplateColumns: 'repeat(3, 1fr)',
+            gap: '1rem',
+            paddingBottom: '1rem',
+          }}
+        >
+          {staticPlans.map((plan) => (
+            <Card
+              key={plan.id}
+              padding="lg"
+              radius="md"
+              withBorder
+              style={{
+                position: 'relative',
+                display: 'flex',
+                flexDirection: 'column',
+                borderColor: plan.id === currentPlan.id ? 'var(--mantine-color-green-6)' : undefined,
+                borderWidth: plan.id === currentPlan.id ? '2px' : undefined,
+              }}
+            >
+              {plan.id === currentPlan.id && (
+                <Badge
+                  color="green"
+                  variant="filled"
+                  size="sm"
+                  style={{ position: 'absolute', top: '1rem', right: '1rem' }}
+                >
+                  {t('plan.current', 'Current Plan')}
+                </Badge>
+              )}
+              {plan.popular && plan.id !== currentPlan.id && (
+                <Badge
+                  variant="filled"
+                  size="xs"
+                  style={{ position: 'absolute', top: '0.5rem', right: '0.5rem' }}
+                >
+                  {t('plan.popular', 'Popular')}
+                </Badge>
+              )}
+
+              <Stack gap="md" style={{ height: '100%' }}>
+                <div>
+                  <Text size="lg" fw={600}>
+                    {plan.name}
+                  </Text>
+                  <Group gap="xs" style={{ alignItems: 'baseline' }}>
+                    <Text size="xl" fw={700} style={{ fontSize: '2rem' }}>
+                      {plan.price === 0 && plan.id !== 'free'
+                        ? t('plan.customPricing', 'Custom')
+                        : plan.price === 0
+                          ? t('plan.free.name', 'Free')
+                          : `${plan.currency}${plan.price}`}
+                    </Text>
+                    {plan.period && (
+                      <Text size="sm" c="dimmed">
+                        {plan.period}
+                      </Text>
+                    )}
+                  </Group>
+                  <Text size="xs" c="dimmed" mt="xs">
+                    {typeof plan.maxUsers === 'string'
+                      ? plan.maxUsers
+                      : `${t('plan.static.upTo', 'Up to')} ${plan.maxUsers} ${t('workspace.people.license.users', 'users')}`}
+                  </Text>
+                </div>
+
+                <Stack gap="xs">
+                  {plan.highlights.map((highlight, index) => (
+                    <Text key={index} size="sm" c="dimmed">
+                      • {highlight}
+                    </Text>
+                  ))}
+                </Stack>
+
+                <div style={{ flexGrow: 1 }} />
+
+                <Button
+                  variant={plan.id === currentPlan.id ? 'light' : 'filled'}
+                  disabled={plan.id === currentPlan.id}
+                  fullWidth
+                  onClick={() =>
+                    window.open('https://www.stirling.com/contact', '_blank')
+                  }
+                >
+                  {plan.id === currentPlan.id
+                    ? t('plan.current', 'Current Plan')
+                    : t('plan.contact', 'Contact Us')}
+                </Button>
+              </Stack>
+            </Card>
+          ))}
+        </div>
+
+        {/* Feature Comparison Toggle */}
+        <div style={{ textAlign: 'center', marginTop: '1rem' }}>
+          <Button variant="subtle" onClick={() => setShowComparison(!showComparison)}>
+            {showComparison
+              ? t('plan.hideComparison', 'Hide Feature Comparison')
+              : t('plan.showComparison', 'Compare All Features')}
+          </Button>
+        </div>
+
+        {/* Feature Comparison Table */}
+        <Collapse in={showComparison}>
+          <FeatureComparisonTable plans={staticPlans} />
+        </Collapse>
+      </div>
+
+      <Divider />
+
+      {/* License Key Section */}
+      <div>
+        <Button
+          variant="subtle"
+          leftSection={<LocalIcon icon={showLicenseKey ? "expand-less-rounded" : "expand-more-rounded"} width="1.25rem" height="1.25rem" />}
+          onClick={() => setShowLicenseKey(!showLicenseKey)}
+        >
+          {t('admin.settings.premium.licenseKey.toggle', 'Got a license key or certificate file?')}
+        </Button>
+
+        <Collapse in={showLicenseKey} mt="md">
+          <Stack gap="md">
+            <Alert
+              variant="light"
+              color="blue"
+              icon={<LocalIcon icon="info-rounded" width="1rem" height="1rem" />}
+            >
+              <Text size="sm">
+                {t('admin.settings.premium.licenseKey.info', 'If you have a license key or certificate file from a direct purchase, you can enter it here to activate premium or enterprise features.')}
+              </Text>
+            </Alert>
+
+            {premiumLoading ? (
+              <Stack align="center" justify="center" h={100}>
+                <Loader size="md" />
+              </Stack>
+            ) : (
+              <Paper withBorder p="md" radius="md">
+                <Stack gap="md">
+                  <div>
+                    <TextInput
+                      label={
+                        <Group gap="xs">
+                          <span>{t('admin.settings.premium.key.label', 'License Key')}</span>
+                          <PendingBadge show={isFieldPending('key')} />
+                        </Group>
+                      }
+                      description={t('admin.settings.premium.key.description', 'Enter your premium or enterprise license key. Premium features will be automatically enabled when a key is provided.')}
+                      value={premiumSettings.key || ''}
+                      onChange={(e) => setPremiumSettings({ ...premiumSettings, key: e.target.value })}
+                      placeholder="00000000-0000-0000-0000-000000000000"
+                    />
+                  </div>
+
+                  <Group justify="flex-end">
+                    <Button onClick={handleSaveLicense} loading={premiumSaving} size="sm">
+                      {t('admin.settings.save', 'Save Changes')}
+                    </Button>
+                  </Group>
+                </Stack>
+              </Paper>
+            )}
+          </Stack>
+        </Collapse>
+      </div>
+
+      {/* Restart Confirmation Modal */}
+      <RestartConfirmationModal
+        opened={restartModalOpened}
+        onClose={closeRestartModal}
+        onRestart={restartServer}
+      />
+    </div>
+  );
+};
+
+export default StaticPlanSection;
diff --git a/frontend/src/proprietary/constants/planConstants.ts b/frontend/src/proprietary/constants/planConstants.ts
new file mode 100644
index 000000000..1865238df
--- /dev/null
+++ b/frontend/src/proprietary/constants/planConstants.ts
@@ -0,0 +1,97 @@
+import { PlanFeature } from '@app/services/licenseService';
+
+/**
+ * Shared plan feature definitions for Stirling PDF Self-Hosted
+ * Used by both dynamic (Stripe) and static (fallback) plan displays
+ */
+
+export const PLAN_FEATURES = {
+  FREE: [
+    { name: 'Self-hosted deployment', included: true },
+    { name: 'All PDF operations', included: true },
+    { name: 'Secure Login Support', included: true },
+    { name: 'Community support', included: true },
+    { name: 'Regular updates', included: true },
+    { name: 'up to 5 users', included: true },
+    { name: 'Unlimited users', included: false },
+    { name: 'Google drive integration', included: false },
+    { name: 'External Database', included: false },
+    { name: 'Editing text in pdfs', included: false },
+    { name: 'Users limited to seats', included: false },
+    { name: 'SSO', included: false },
+    { name: 'Auditing', included: false },
+    { name: 'Usage tracking', included: false },
+    { name: 'Prometheus Support', included: false },
+    { name: 'Custom PDF metadata', included: false },
+  ] as PlanFeature[],
+
+  SERVER: [
+    { name: 'Self-hosted deployment', included: true },
+    { name: 'All PDF operations', included: true },
+    { name: 'Secure Login Support', included: true },
+    { name: 'Community support', included: true },
+    { name: 'Regular updates', included: true },
+    { name: 'Up to 5 users', included: false },
+    { name: 'Unlimited users', included: true },
+    { name: 'Google drive integration', included: true },
+    { name: 'External Database', included: true },
+    { name: 'Editing text in pdfs', included: true },
+    { name: 'Users limited to seats', included: false },
+    { name: 'SSO', included: false },
+    { name: 'Auditing', included: false },
+    { name: 'Usage tracking', included: false },
+    { name: 'Prometheus Support', included: false },
+    { name: 'Custom PDF metadata', included: false },
+  ] as PlanFeature[],
+
+  ENTERPRISE: [
+    { name: 'Self-hosted deployment', included: true },
+    { name: 'All PDF operations', included: true },
+    { name: 'Secure Login Support', included: true },
+    { name: 'Community support', included: true },
+    { name: 'Regular updates', included: true },
+    { name: 'up to 5 users', included: false },
+    { name: 'Unlimited users', included: false },
+    { name: 'Google drive integration', included: true },
+    { name: 'External Database', included: true },
+    { name: 'Editing text in pdfs', included: true },
+    { name: 'Users limited to seats', included: true },
+    { name: 'SSO', included: true },
+    { name: 'Auditing', included: true },
+    { name: 'Usage tracking', included: true },
+    { name: 'Prometheus Support', included: true },
+    { name: 'Custom PDF metadata', included: true },
+  ] as PlanFeature[],
+} as const;
+
+export const PLAN_HIGHLIGHTS = {
+  FREE: [
+    'Up to 5 users',
+    'Self-hosted',
+    'All basic features'
+  ],
+  SERVER_MONTHLY: [
+    'Self-hosted on your infrastructure',
+    'Unlimited users',
+    'Advanced integrations',
+    'Cancel anytime'
+  ],
+  SERVER_YEARLY: [
+    'Self-hosted on your infrastructure',
+    'Unlimited users',
+    'Advanced integrations',
+    'Save with annual billing'
+  ],
+  ENTERPRISE_MONTHLY: [
+    'Enterprise features (SSO, Auditing)',
+    'Usage tracking & Prometheus',
+    'Custom PDF metadata',
+    'Per-seat licensing'
+  ],
+  ENTERPRISE_YEARLY: [
+    'Enterprise features (SSO, Auditing)',
+    'Usage tracking & Prometheus',
+    'Custom PDF metadata',
+    'Save with annual billing'
+  ]
+} as const;
diff --git a/frontend/src/proprietary/contexts/CheckoutContext.tsx b/frontend/src/proprietary/contexts/CheckoutContext.tsx
new file mode 100644
index 000000000..f8558a650
--- /dev/null
+++ b/frontend/src/proprietary/contexts/CheckoutContext.tsx
@@ -0,0 +1,350 @@
+import React, { createContext, useContext, useState, useCallback, useEffect, ReactNode } from 'react';
+import { useTranslation } from 'react-i18next';
+import { usePlans } from '@app/hooks/usePlans';
+import licenseService, { PlanTierGroup, LicenseInfo, mapLicenseToTier } from '@app/services/licenseService';
+import StripeCheckout from '@app/components/shared/StripeCheckout';
+import { userManagementService } from '@app/services/userManagementService';
+import { alert } from '@app/components/toast';
+import { pollLicenseKeyWithBackoff, activateLicenseKey, resyncExistingLicense } from '@app/utils/licenseCheckoutUtils';
+import { useLicense } from '@app/contexts/LicenseContext';
+import { isSupabaseConfigured } from '@app/services/supabaseClient';
+
+export interface CheckoutOptions {
+  minimumSeats?: number;      // Override calculated seats for enterprise
+  currency?: string;          // Optional currency override (defaults to 'gbp')
+  onSuccess?: (sessionId: string) => void;  // Callback after successful payment
+  onError?: (error: string) => void;  // Callback on error
+}
+
+interface CheckoutContextValue {
+  openCheckout: (
+    tier: 'server' | 'enterprise',
+    options?: CheckoutOptions
+  ) => Promise<void>;
+  closeCheckout: () => void;
+  isOpen: boolean;
+  isLoading: boolean;
+}
+
+const CheckoutContext = createContext<CheckoutContextValue | undefined>(undefined);
+
+interface CheckoutProviderProps {
+  children: ReactNode;
+  defaultCurrency?: string;
+}
+
+export const CheckoutProvider: React.FC<CheckoutProviderProps> = ({
+  children,
+  defaultCurrency = 'gbp'
+}) => {
+  const { t } = useTranslation();
+  const { refetchLicense } = useLicense();
+  const [isOpen, setIsOpen] = useState(false);
+  const [isLoading, setIsLoading] = useState(false);
+  const [selectedPlanGroup, setSelectedPlanGroup] = useState<PlanTierGroup | null>(null);
+  const [minimumSeats, setMinimumSeats] = useState<number>(1);
+  const [currentCurrency, setCurrentCurrency] = useState(defaultCurrency);
+  const [currentOptions, setCurrentOptions] = useState<CheckoutOptions>({});
+  const [hostedCheckoutSuccess, setHostedCheckoutSuccess] = useState<{
+    isUpgrade: boolean;
+    licenseKey?: string;
+  } | null>(null);
+
+  // Load plans with current currency
+  const { plans, refetch: refetchPlans } = usePlans(currentCurrency);
+
+  // Handle return from hosted Stripe checkout
+  useEffect(() => {
+    const handleCheckoutReturn = async () => {
+      const urlParams = new URLSearchParams(window.location.search);
+      const paymentStatus = urlParams.get('payment_status');
+      const sessionId = urlParams.get('session_id');
+
+      if (paymentStatus === 'success' && sessionId) {
+        console.log('Payment successful via hosted checkout:', sessionId);
+
+        // Clear URL parameters
+        window.history.replaceState({}, '', window.location.pathname);
+
+        // Fetch current license info to determine upgrade vs new
+        let licenseInfo: LicenseInfo | null = null;
+        try {
+          licenseInfo = await licenseService.getLicenseInfo();
+        } catch (err) {
+          console.warn('Could not fetch license info:', err);
+        }
+
+        // Check if this is an upgrade or new subscription
+        if (licenseInfo?.licenseKey) {
+          // UPGRADE: Resync existing license with Keygen
+          console.log('Upgrade detected - resyncing existing license');
+
+          const activation = await resyncExistingLicense();
+
+          if (activation.success) {
+            console.log('License synced successfully, refreshing license context');
+
+            // Refresh global license context
+            await refetchLicense();
+            await refetchPlans();
+
+            // Determine tier from license type
+            const tier = activation.licenseType === 'ENTERPRISE' ? 'enterprise' : 'server';
+            const planGroups = licenseService.groupPlansByTier(plans);
+            const planGroup = planGroups.find(pg => pg.tier === tier);
+
+            if (planGroup) {
+              // Reopen modal to show success
+              setSelectedPlanGroup(planGroup);
+              setHostedCheckoutSuccess({ isUpgrade: true });
+              setIsOpen(true);
+            } else {
+              // Fallback to toast if plan group not found
+              alert({
+                alertType: 'success',
+                title: t('payment.upgradeSuccess'),
+              });
+            }
+          } else {
+            console.error('Failed to sync license after upgrade:', activation.error);
+            alert({
+              alertType: 'error',
+              title: t('payment.syncError'),
+            });
+          }
+        } else {
+          // NEW SUBSCRIPTION: Poll for license key
+          console.log('New subscription - polling for license key');
+
+          try {
+            const installationId = await licenseService.getInstallationId();
+            console.log('Polling for license key with installation ID:', installationId);
+
+            // Use shared polling utility
+            const result = await pollLicenseKeyWithBackoff(installationId);
+
+            if (result.success && result.licenseKey) {
+              // Activate the license key
+              const activation = await activateLicenseKey(result.licenseKey);
+
+              if (activation.success) {
+                console.log(`License key activated: ${activation.licenseType}`);
+
+                // Refresh global license context
+                await refetchLicense();
+                await refetchPlans();
+
+                // Determine tier from license type
+                const tier = activation.licenseType === 'ENTERPRISE' ? 'enterprise' : 'server';
+                const planGroups = licenseService.groupPlansByTier(plans);
+                const planGroup = planGroups.find(pg => pg.tier === tier);
+
+                if (planGroup) {
+                  // Reopen modal to show success with license key
+                  setSelectedPlanGroup(planGroup);
+                  setHostedCheckoutSuccess({
+                    isUpgrade: false,
+                    licenseKey: result.licenseKey
+                  });
+                  setIsOpen(true);
+                } else {
+                  // Fallback to toast if plan group not found
+                  alert({
+                    alertType: 'success',
+                    title: t('payment.licenseActivated'),
+                  });
+                }
+              } else {
+                console.error('Failed to save license key:', activation.error);
+                alert({
+                  alertType: 'error',
+                  title: t('payment.licenseSaveError'),
+                });
+              }
+            } else if (result.timedOut) {
+              console.warn('License key polling timed out');
+              alert({
+                alertType: 'warning',
+                title: t('payment.licenseDelayed'),
+              });
+            } else {
+              console.error('License key polling failed:', result.error);
+              alert({
+                alertType: 'error',
+                title: t('payment.licensePollingError'),
+              });
+            }
+          } catch (error) {
+            console.error('Failed to poll for license key:', error);
+            alert({
+              alertType: 'error',
+              title: t('payment.licenseRetrievalError'),
+            });
+          }
+        }
+      } else if (paymentStatus === 'canceled') {
+        console.log('Payment canceled by user');
+
+        // Clear URL parameters
+        window.history.replaceState({}, '', window.location.pathname);
+
+        alert({
+          alertType: 'warning',
+          title: t('payment.paymentCanceled'),
+        });
+      }
+    };
+
+    handleCheckoutReturn();
+  }, [t, refetchPlans, refetchLicense, plans]);
+
+  const openCheckout = useCallback(
+    async (tier: 'server' | 'enterprise', options: CheckoutOptions = {}) => {
+      try {
+        setIsLoading(true);
+
+        // Check if Supabase is configured
+        if (!isSupabaseConfigured) {
+          throw new Error('Checkout is not available. Supabase is not configured.');
+        }
+
+        // Update currency if provided
+        const currency = options.currency || currentCurrency;
+        if (currency !== currentCurrency) {
+          setCurrentCurrency(currency);
+          // Plans will reload automatically via usePlans
+        }
+
+        // Fetch license info and user data for seat calculations
+        let licenseInfo: LicenseInfo | null = null;
+        let totalUsers = 0;
+
+        try {
+          const [licenseData, userData] = await Promise.all([
+            licenseService.getLicenseInfo(),
+            userManagementService.getUsers()
+          ]);
+
+          licenseInfo = licenseData;
+          totalUsers = userData.totalUsers || 0;
+        } catch (err) {
+          console.warn('Could not fetch license/user info, proceeding with defaults:', err);
+        }
+
+        // Calculate minimum seats for enterprise upgrades
+        let calculatedMinSeats = options.minimumSeats || 1;
+
+        if (tier === 'enterprise' && !options.minimumSeats) {
+          const currentTier = mapLicenseToTier(licenseInfo);
+
+          if (currentTier === 'server' || currentTier === 'free') {
+            // Upgrading from Server (unlimited) to Enterprise (per-seat)
+            // Use current total user count as minimum
+            calculatedMinSeats = Math.max(totalUsers, 1);
+            console.log(`Setting minimum seats from server user count: ${calculatedMinSeats}`);
+          } else if (currentTier === 'enterprise') {
+            // Upgrading within Enterprise (e.g., monthly to yearly)
+            // Use current licensed seat count as minimum
+            calculatedMinSeats = Math.max(licenseInfo?.maxUsers || 1, 1);
+            console.log(`Setting minimum seats from current license: ${calculatedMinSeats}`);
+          }
+        }
+
+        // Find the plan group for the requested tier
+        const planGroups = licenseService.groupPlansByTier(plans);
+        const planGroup = planGroups.find(pg => pg.tier === tier);
+
+        if (!planGroup) {
+          throw new Error(`No ${tier} plan available`);
+        }
+
+        // Store options for callbacks
+        setCurrentOptions(options);
+        setMinimumSeats(calculatedMinSeats);
+        setSelectedPlanGroup(planGroup);
+        setIsOpen(true);
+
+      } catch (err) {
+        const errorMessage = err instanceof Error ? err.message : 'Failed to open checkout';
+        console.error('Error opening checkout:', errorMessage);
+        options.onError?.(errorMessage);
+      } finally {
+        setIsLoading(false);
+      }
+    },
+    [currentCurrency, plans]
+  );
+
+  const closeCheckout = useCallback(() => {
+    setIsOpen(false);
+    setSelectedPlanGroup(null);
+    setCurrentOptions({});
+    setHostedCheckoutSuccess(null);
+
+    // Refetch plans and license after modal closes to update subscription display
+    refetchPlans();
+    refetchLicense();
+  }, [refetchPlans, refetchLicense]);
+
+  const handlePaymentSuccess = useCallback(
+    (sessionId: string) => {
+      console.log('Payment successful, session:', sessionId);
+      currentOptions.onSuccess?.(sessionId);
+      // Don't close modal - let user view license key and close manually
+    },
+    [currentOptions]
+  );
+
+  const handlePaymentError = useCallback(
+    (error: string) => {
+      console.error('Payment error:', error);
+      currentOptions.onError?.(error);
+    },
+    [currentOptions]
+  );
+
+  const handleLicenseActivated = useCallback((licenseInfo: {
+    licenseType: string;
+    enabled: boolean;
+    maxUsers: number;
+    hasKey: boolean;
+  }) => {
+    console.log('License activated:', licenseInfo);
+    // Could expose this via context if needed
+  }, []);
+
+  const contextValue: CheckoutContextValue = {
+    openCheckout,
+    closeCheckout,
+    isOpen,
+    isLoading,
+  };
+
+  return (
+    <CheckoutContext.Provider value={contextValue}>
+      {children}
+
+      {/* Global Checkout Modal */}
+      {selectedPlanGroup && (
+        <StripeCheckout
+          opened={isOpen}
+          onClose={closeCheckout}
+          planGroup={selectedPlanGroup}
+          minimumSeats={minimumSeats}
+          onSuccess={handlePaymentSuccess}
+          onError={handlePaymentError}
+          onLicenseActivated={handleLicenseActivated}
+          hostedCheckoutSuccess={hostedCheckoutSuccess}
+        />
+      )}
+    </CheckoutContext.Provider>
+  );
+};
+
+export const useCheckout = (): CheckoutContextValue => {
+  const context = useContext(CheckoutContext);
+  if (!context) {
+    throw new Error('useCheckout must be used within CheckoutProvider');
+  }
+  return context;
+};
diff --git a/frontend/src/proprietary/contexts/LicenseContext.tsx b/frontend/src/proprietary/contexts/LicenseContext.tsx
new file mode 100644
index 000000000..9414dcf5d
--- /dev/null
+++ b/frontend/src/proprietary/contexts/LicenseContext.tsx
@@ -0,0 +1,74 @@
+import React, { createContext, useContext, useState, useCallback, useEffect, ReactNode } from 'react';
+import licenseService, { LicenseInfo } from '@app/services/licenseService';
+import { useAppConfig } from '@app/contexts/AppConfigContext';
+
+interface LicenseContextValue {
+  licenseInfo: LicenseInfo | null;
+  loading: boolean;
+  error: string | null;
+  refetchLicense: () => Promise<void>;
+}
+
+const LicenseContext = createContext<LicenseContextValue | undefined>(undefined);
+
+interface LicenseProviderProps {
+  children: ReactNode;
+}
+
+export const LicenseProvider: React.FC<LicenseProviderProps> = ({ children }) => {
+  const { config } = useAppConfig();
+  const [licenseInfo, setLicenseInfo] = useState<LicenseInfo | null>(null);
+  const [loading, setLoading] = useState<boolean>(true);
+  const [error, setError] = useState<string | null>(null);
+
+  const refetchLicense = useCallback(async () => {
+    // Only fetch license info if user is an admin
+    if (!config?.isAdmin) {
+      console.debug('[LicenseContext] User is not an admin, skipping license fetch');
+      setLoading(false);
+      return;
+    }
+
+    try {
+      setLoading(true);
+      setError(null);
+      const info = await licenseService.getLicenseInfo();
+      setLicenseInfo(info);
+    } catch (err) {
+      const errorMessage = err instanceof Error ? err.message : 'Failed to fetch license info';
+      console.error('Error fetching license info:', errorMessage);
+      setError(errorMessage);
+      setLicenseInfo(null);
+    } finally {
+      setLoading(false);
+    }
+  }, [config?.isAdmin]);
+
+  // Fetch license info when config changes (only if user is admin)
+  useEffect(() => {
+    if (config) {
+      refetchLicense();
+    }
+  }, [config, refetchLicense]);
+
+  const contextValue: LicenseContextValue = {
+    licenseInfo,
+    loading,
+    error,
+    refetchLicense,
+  };
+
+  return (
+    <LicenseContext.Provider value={contextValue}>
+      {children}
+    </LicenseContext.Provider>
+  );
+};
+
+export const useLicense = (): LicenseContextValue => {
+  const context = useContext(LicenseContext);
+  if (!context) {
+    throw new Error('useLicense must be used within LicenseProvider');
+  }
+  return context;
+};
diff --git a/frontend/src/proprietary/hooks/usePlans.ts b/frontend/src/proprietary/hooks/usePlans.ts
new file mode 100644
index 000000000..33cb198de
--- /dev/null
+++ b/frontend/src/proprietary/hooks/usePlans.ts
@@ -0,0 +1,44 @@
+import { useState, useEffect } from 'react';
+import licenseService, {
+  PlanTier,
+  PlansResponse,
+} from '@app/services/licenseService';
+
+export interface UsePlansReturn {
+  plans: PlanTier[];
+  loading: boolean;
+  error: string | null;
+  refetch: () => Promise<void>;
+}
+
+export const usePlans = (currency: string = 'gbp'): UsePlansReturn => {
+  const [plans, setPlans] = useState<PlanTier[]>([]);
+  const [loading, setLoading] = useState(true);
+  const [error, setError] = useState<string | null>(null);
+
+  const fetchPlans = async () => {
+    try {
+      setLoading(true);
+      setError(null);
+
+      const data: PlansResponse = await licenseService.getPlans(currency);
+      setPlans(data.plans);
+    } catch (err) {
+      console.error('Error fetching plans:', err);
+      setError(err instanceof Error ? err.message : 'Failed to fetch plans');
+    } finally {
+      setLoading(false);
+    }
+  };
+
+  useEffect(() => {
+    fetchPlans();
+  }, [currency]);
+
+  return {
+    plans,
+    loading,
+    error,
+    refetch: fetchPlans,
+  };
+};
diff --git a/frontend/src/proprietary/services/licenseService.ts b/frontend/src/proprietary/services/licenseService.ts
new file mode 100644
index 000000000..409dbfd74
--- /dev/null
+++ b/frontend/src/proprietary/services/licenseService.ts
@@ -0,0 +1,475 @@
+import apiClient from '@app/services/apiClient';
+import { supabase, isSupabaseConfigured } from '@app/services/supabaseClient';
+import { getCheckoutMode } from '@app/utils/protocolDetection';
+import { PLAN_FEATURES, PLAN_HIGHLIGHTS } from '@app/constants/planConstants';
+
+export interface PlanFeature {
+  name: string;
+  included: boolean;
+}
+
+export interface PlanTier {
+  id: string;
+  name: string;
+  price: number;
+  currency: string;
+  period: string;
+  popular?: boolean;
+  features: PlanFeature[];
+  highlights: readonly string[];
+  isContactOnly?: boolean;
+  seatPrice?: number;        // Per-seat price for enterprise plans
+  requiresSeats?: boolean;   // Flag indicating seat selection is needed
+  lookupKey: string;         // Stripe lookup key for this plan
+}
+
+export interface PlanTierGroup {
+  tier: 'free' | 'server' | 'enterprise';
+  name: string;
+  monthly: PlanTier | null;
+  yearly: PlanTier | null;
+  features: PlanFeature[];
+  highlights: readonly string[];
+  popular?: boolean;
+}
+
+export interface PlansResponse {
+  plans: PlanTier[];
+}
+
+export interface CheckoutSessionRequest {
+  lookup_key: string;       // Stripe lookup key (e.g., 'selfhosted:server:monthly')
+  installation_id?: string; // Installation ID from backend (MAC-based fingerprint)
+  current_license_key?: string; // Current license key for upgrades
+  requires_seats?: boolean; // Whether to add adjustable seat pricing
+  seat_count?: number;      // Initial number of seats for enterprise plans (user can adjust in Stripe UI)
+  successUrl?: string;
+  cancelUrl?: string;
+}
+
+export interface CheckoutSessionResponse {
+  clientSecret: string;
+  sessionId: string;
+  url?: string;  // URL for hosted checkout (when not using HTTPS)
+}
+
+export interface BillingPortalResponse {
+  url: string;
+}
+
+export interface InstallationIdResponse {
+  installationId: string;
+}
+
+export interface LicenseKeyResponse {
+  status: 'ready' | 'pending';
+  license_key?: string;
+  email?: string;
+  plan?: string;
+}
+
+export interface LicenseInfo {
+  licenseType: 'NORMAL' | 'PRO' | 'ENTERPRISE';
+  enabled: boolean;
+  maxUsers: number;
+  hasKey: boolean;
+  licenseKey?: string; // The actual license key (for upgrades)
+}
+
+export interface LicenseSaveResponse {
+  success: boolean;
+  licenseType?: string;
+  message?: string;
+  error?: string;
+}
+
+// Currency symbol mapping
+const getCurrencySymbol = (currency: string): string => {
+  const currencySymbols: { [key: string]: string } = {
+    'gbp': '£',
+    'usd': '$',
+    'eur': '€',
+    'cny': '¥',
+    'inr': '₹',
+    'brl': 'R$',
+    'idr': 'Rp'
+  };
+  return currencySymbols[currency.toLowerCase()] || currency.toUpperCase();
+};
+
+// Self-hosted plan lookup keys
+const SELF_HOSTED_LOOKUP_KEYS = [
+  'selfhosted:server:monthly',
+  'selfhosted:server:yearly',
+  'selfhosted:enterpriseseat:monthly',
+  'selfhosted:enterpriseseat:yearly',
+];
+
+const licenseService = {
+  /**
+   * Get available plans with pricing for the specified currency
+   */
+  async getPlans(currency: string = 'gbp'): Promise<PlansResponse> {
+    try {
+      // Check if Supabase is configured
+      if (!isSupabaseConfigured || !supabase) {
+        throw new Error('Supabase is not configured. Please use static plans instead.');
+      }
+
+      // Fetch all self-hosted prices from Stripe
+      const { data, error } = await supabase.functions.invoke<{
+        prices: Record<string, {
+          unit_amount: number;
+          currency: string;
+          lookup_key: string;
+        }>;
+        missing: string[];
+      }>('stripe-price-lookup', {
+        body: {
+          lookup_keys: SELF_HOSTED_LOOKUP_KEYS,
+          currency
+        },
+      });
+
+      if (error) {
+        throw new Error(`Failed to fetch plans: ${error.message}`);
+      }
+
+      if (!data || !data.prices) {
+        throw new Error('No pricing data returned');
+      }
+
+      // Log missing prices for debugging
+      if (data.missing && data.missing.length > 0) {
+        console.warn('Missing Stripe prices for lookup keys:', data.missing, 'in currency:', currency);
+      }
+
+      // Build price map for easy access
+      const priceMap = new Map<string, { unit_amount: number; currency: string }>();
+      for (const [lookupKey, priceData] of Object.entries(data.prices)) {
+        priceMap.set(lookupKey, {
+          unit_amount: priceData.unit_amount,
+          currency: priceData.currency
+        });
+      }
+
+      const currencySymbol = getCurrencySymbol(currency);
+
+      // Helper to get price info
+      const getPriceInfo = (lookupKey: string, fallback: number = 0) => {
+        const priceData = priceMap.get(lookupKey);
+        return priceData ? priceData.unit_amount / 100 : fallback;
+      };
+
+      // Build plan tiers
+      const plans: PlanTier[] = [
+        {
+          id: 'selfhosted:server:monthly',
+          lookupKey: 'selfhosted:server:monthly',
+          name: 'Server - Monthly',
+          price: getPriceInfo('selfhosted:server:monthly'),
+          currency: currencySymbol,
+          period: '/month',
+          popular: false,
+          features: PLAN_FEATURES.SERVER,
+          highlights: PLAN_HIGHLIGHTS.SERVER_MONTHLY
+        },
+        {
+          id: 'selfhosted:server:yearly',
+          lookupKey: 'selfhosted:server:yearly',
+          name: 'Server - Yearly',
+          price: getPriceInfo('selfhosted:server:yearly'),
+          currency: currencySymbol,
+          period: '/year',
+          popular: true,
+          features: PLAN_FEATURES.SERVER,
+          highlights: PLAN_HIGHLIGHTS.SERVER_YEARLY
+        },
+        {
+          id: 'selfhosted:enterprise:monthly',
+          lookupKey: 'selfhosted:server:monthly',
+          name: 'Enterprise - Monthly',
+          price: getPriceInfo('selfhosted:server:monthly'),
+          seatPrice: getPriceInfo('selfhosted:enterpriseseat:monthly'),
+          currency: currencySymbol,
+          period: '/month',
+          popular: false,
+          requiresSeats: true,
+          features: PLAN_FEATURES.ENTERPRISE,
+          highlights: PLAN_HIGHLIGHTS.ENTERPRISE_MONTHLY
+        },
+        {
+          id: 'selfhosted:enterprise:yearly',
+          lookupKey: 'selfhosted:server:yearly',
+          name: 'Enterprise - Yearly',
+          price: getPriceInfo('selfhosted:server:yearly'),
+          seatPrice: getPriceInfo('selfhosted:enterpriseseat:yearly'),
+          currency: currencySymbol,
+          period: '/year',
+          popular: false,
+          requiresSeats: true,
+          features: PLAN_FEATURES.ENTERPRISE,
+          highlights: PLAN_HIGHLIGHTS.ENTERPRISE_YEARLY
+        },
+      ];
+
+      // Filter out plans with missing prices (price === 0 means Stripe price not found)
+      const validPlans = plans.filter(plan => plan.price > 0);
+
+      if (validPlans.length < plans.length) {
+        const missingPlans = plans.filter(plan => plan.price === 0).map(p => p.id);
+        console.warn('Filtered out plans with missing prices:', missingPlans);
+      }
+
+      // Add Free plan (static definition)
+      const freePlan: PlanTier = {
+        id: 'free',
+        lookupKey: 'free',
+        name: 'Free',
+        price: 0,
+        currency: currencySymbol,
+        period: '',
+        popular: false,
+        features: PLAN_FEATURES.FREE,
+        highlights: PLAN_HIGHLIGHTS.FREE
+      };
+
+      const allPlans = [freePlan, ...validPlans];
+
+      return {
+        plans: allPlans
+      };
+    } catch (error) {
+      console.error('Error fetching plans:', error);
+      throw error;
+    }
+  },
+
+  /**
+   * Group plans by tier for display (Free, Server, Enterprise)
+   */
+  groupPlansByTier(plans: PlanTier[]): PlanTierGroup[] {
+    const groups: PlanTierGroup[] = [];
+
+    // Free tier
+    const freePlan = plans.find(p => p.id === 'free');
+    if (freePlan) {
+      groups.push({
+        tier: 'free',
+        name: 'Free',
+        monthly: freePlan,
+        yearly: null,
+        features: freePlan.features,
+        highlights: freePlan.highlights,
+        popular: false,
+      });
+    }
+
+    // Server tier
+    const serverMonthly = plans.find(p => p.lookupKey === 'selfhosted:server:monthly');
+    const serverYearly = plans.find(p => p.lookupKey === 'selfhosted:server:yearly');
+    if (serverMonthly || serverYearly) {
+      groups.push({
+        tier: 'server',
+        name: 'Server',
+        monthly: serverMonthly || null,
+        yearly: serverYearly || null,
+        features: (serverMonthly || serverYearly)!.features,
+        highlights: (serverMonthly || serverYearly)!.highlights,
+        popular: serverYearly?.popular || serverMonthly?.popular || false,
+      });
+    }
+
+    // Enterprise tier (uses server pricing + seats)
+    const enterpriseMonthly = plans.find(p => p.id === 'selfhosted:enterprise:monthly');
+    const enterpriseYearly = plans.find(p => p.id === 'selfhosted:enterprise:yearly');
+    if (enterpriseMonthly || enterpriseYearly) {
+      groups.push({
+        tier: 'enterprise',
+        name: 'Enterprise',
+        monthly: enterpriseMonthly || null,
+        yearly: enterpriseYearly || null,
+        features: (enterpriseMonthly || enterpriseYearly)!.features,
+        highlights: (enterpriseMonthly || enterpriseYearly)!.highlights,
+        popular: false,
+      });
+    }
+
+    return groups;
+  },
+
+  /**
+   * Create a Stripe checkout session for upgrading
+   */
+  async createCheckoutSession(request: CheckoutSessionRequest): Promise<CheckoutSessionResponse> {
+    // Check if Supabase is configured
+    if (!isSupabaseConfigured || !supabase) {
+      throw new Error('Supabase is not configured. Checkout is not available.');
+    }
+
+    // Detect if HTTPS is available to determine checkout mode
+    const checkoutMode = getCheckoutMode();
+    const baseUrl = window.location.origin;
+    const settingsUrl = `${baseUrl}/settings/adminPlan`;
+
+    const { data, error } = await supabase.functions.invoke('create-checkout', {
+      body: {
+        self_hosted: true,
+        lookup_key: request.lookup_key,
+        installation_id: request.installation_id,
+        current_license_key: request.current_license_key,
+        requires_seats: request.requires_seats,
+        seat_count: request.seat_count || 1,
+        callback_base_url: baseUrl,
+        ui_mode: checkoutMode,
+        // For hosted checkout, provide success/cancel URLs
+        success_url: checkoutMode === 'hosted'
+          ? `${settingsUrl}?session_id={CHECKOUT_SESSION_ID}&payment_status=success`
+          : undefined,
+        cancel_url: checkoutMode === 'hosted'
+          ? `${settingsUrl}?payment_status=canceled`
+          : undefined,
+      },
+    });
+
+    if (error) {
+      throw new Error(`Failed to create checkout session: ${error.message}`);
+    }
+
+    return data as CheckoutSessionResponse;
+  },
+
+  /**
+   * Create a Stripe billing portal session for managing subscription
+   * Uses license key for self-hosted authentication
+   */
+  async createBillingPortalSession(returnUrl: string, licenseKey: string): Promise<BillingPortalResponse> {
+    // Check if Supabase is configured
+    if (!isSupabaseConfigured || !supabase) {
+      throw new Error('Supabase is not configured. Billing portal is not available.');
+    }
+
+    const { data, error} = await supabase.functions.invoke('manage-billing', {
+      body: {
+        return_url: returnUrl,
+        license_key: licenseKey,
+        self_hosted: true  // Explicitly indicate self-hosted mode
+      },
+    });
+
+    if (error) {
+      throw new Error(`Failed to create billing portal session: ${error.message}`);
+    }
+
+    return data as BillingPortalResponse;
+  },
+
+  /**
+   * Get the installation ID from the backend (MAC-based fingerprint)
+   */
+  async getInstallationId(): Promise<string> {
+    try {
+      const response = await apiClient.get('/api/v1/admin/installation-id');
+
+      const data: InstallationIdResponse = await response.data;
+      return data.installationId;
+    } catch (error) {
+      console.error('Error fetching installation ID:', error);
+      throw error;
+    }
+  },
+
+  /**
+   * Check if license key is ready for the given installation ID
+   */
+  async checkLicenseKey(installationId: string): Promise<LicenseKeyResponse> {
+    // Check if Supabase is configured
+    if (!isSupabaseConfigured || !supabase) {
+      throw new Error('Supabase is not configured. License key lookup is not available.');
+    }
+
+    const { data, error } = await supabase.functions.invoke('get-license-key', {
+      body: {
+        installation_id: installationId,
+      },
+    });
+
+    if (error) {
+      throw new Error(`Failed to check license key: ${error.message}`);
+    }
+
+    return data as LicenseKeyResponse;
+  },
+
+  /**
+   * Save license key to backend
+   */
+  async saveLicenseKey(licenseKey: string): Promise<LicenseSaveResponse> {
+    try {
+      const response = await apiClient.post('/api/v1/admin/license-key', {
+        licenseKey: licenseKey,
+      });
+
+      return response.data;
+    } catch (error) {
+      console.error('Error saving license key:', error);
+      throw error;
+    }
+  },
+
+  /**
+   * Get current license information from backend
+   */
+  async getLicenseInfo(): Promise<LicenseInfo> {
+    try {
+      const response = await apiClient.get('/api/v1/admin/license-info');
+      return response.data;
+    } catch (error) {
+      console.error('Error fetching license info:', error);
+      throw error;
+    }
+  },
+
+  /**
+   * Resync the current license with Keygen
+   * Re-validates the existing license key and updates local settings
+   */
+  async resyncLicense(): Promise<LicenseSaveResponse> {
+    try {
+      const response = await apiClient.post('/api/v1/admin/license/resync');
+      return response.data;
+    } catch (error) {
+      console.error('Error resyncing license:', error);
+      throw error;
+    }
+  },
+};
+
+/**
+ * Map license type to plan tier
+ * @param licenseInfo - Current license information
+ * @returns Plan tier: 'free' | 'server' | 'enterprise'
+ */
+export const mapLicenseToTier = (licenseInfo: LicenseInfo | null): 'free' | 'server' | 'enterprise' | null => {
+  if (!licenseInfo) return null;
+
+  // No license or NORMAL type = Free tier
+  if (licenseInfo.licenseType === 'NORMAL' || !licenseInfo.enabled) {
+    return 'free';
+  }
+
+  // PRO type (no seats) = Server tier
+  if (licenseInfo.licenseType === 'PRO') {
+    return 'server';
+  }
+
+  // ENTERPRISE type (with seats) = Enterprise tier
+  if (licenseInfo.licenseType === 'ENTERPRISE' && licenseInfo.maxUsers > 0) {
+    return 'enterprise';
+  }
+
+  // Default fallback
+  return 'free';
+};
+
+export default licenseService;
diff --git a/frontend/src/proprietary/utils/licenseCheckoutUtils.ts b/frontend/src/proprietary/utils/licenseCheckoutUtils.ts
new file mode 100644
index 000000000..6235bbfe9
--- /dev/null
+++ b/frontend/src/proprietary/utils/licenseCheckoutUtils.ts
@@ -0,0 +1,265 @@
+/**
+ * Shared utilities for license checkout completion
+ * Used by both embedded and hosted checkout flows
+ */
+
+import licenseService, { LicenseInfo } from '@app/services/licenseService';
+
+/**
+ * Result of license key polling
+ */
+export interface LicenseKeyPollResult {
+  success: boolean;
+  licenseKey?: string;
+  error?: string;
+  timedOut?: boolean;
+}
+
+/**
+ * Configuration for license key polling
+ */
+export interface PollConfig {
+  /** Check if component is still mounted (prevents state updates after unmount) */
+  isMounted?: () => boolean;
+  /** Callback for status changes during polling */
+  onStatusChange?: (status: 'polling' | 'ready' | 'timeout') => void;
+  /** Custom backoff intervals in milliseconds (default: [1000, 2000, 4000, 8000, 16000]) */
+  backoffMs?: number[];
+}
+
+/**
+ * Poll for license key with exponential backoff
+ * Consolidates polling logic used by both embedded and hosted checkout
+ */
+export async function pollLicenseKeyWithBackoff(
+  installationId: string,
+  config: PollConfig = {}
+): Promise<LicenseKeyPollResult> {
+  const {
+    isMounted = () => true,
+    onStatusChange,
+    backoffMs = [1000, 2000, 4000, 8000, 16000],
+  } = config;
+
+  let attemptIndex = 0;
+
+  onStatusChange?.('polling');
+  console.log(`Starting license key polling for installation: ${installationId}`);
+
+  const poll = async (): Promise<LicenseKeyPollResult> => {
+    // Check if component is still mounted
+    if (!isMounted()) {
+      console.log('Polling cancelled: component unmounted');
+      return { success: false, error: 'Component unmounted' };
+    }
+
+    const attemptNumber = attemptIndex + 1;
+    console.log(`Polling attempt ${attemptNumber}/${backoffMs.length}`);
+
+    try {
+      const response = await licenseService.checkLicenseKey(installationId);
+
+      // Check mounted after async operation
+      if (!isMounted()) {
+        return { success: false, error: 'Component unmounted' };
+      }
+
+      if (response.status === 'ready' && response.license_key) {
+        console.log('✅ License key ready!');
+        onStatusChange?.('ready');
+        return {
+          success: true,
+          licenseKey: response.license_key,
+        };
+      }
+
+      // License not ready yet, continue polling
+      attemptIndex++;
+
+      if (attemptIndex >= backoffMs.length) {
+        console.warn('⏱️ License polling timeout after all attempts');
+        onStatusChange?.('timeout');
+        return {
+          success: false,
+          timedOut: true,
+          error: 'Polling timeout - license key not ready',
+        };
+      }
+
+      // Wait before next attempt
+      const nextDelay = backoffMs[attemptIndex];
+      console.log(`Retrying in ${nextDelay}ms...`);
+      await new Promise(resolve => setTimeout(resolve, nextDelay));
+
+      return poll();
+    } catch (error) {
+      console.error(`Polling attempt ${attemptNumber} failed:`, error);
+
+      if (!isMounted()) {
+        return { success: false, error: 'Component unmounted' };
+      }
+
+      attemptIndex++;
+
+      if (attemptIndex >= backoffMs.length) {
+        console.error('Polling failed after all attempts');
+        onStatusChange?.('timeout');
+        return {
+          success: false,
+          error: error instanceof Error ? error.message : 'Polling failed',
+        };
+      }
+
+      // Retry with exponential backoff even on error
+      const nextDelay = backoffMs[attemptIndex];
+      console.log(`Retrying after error in ${nextDelay}ms...`);
+      await new Promise(resolve => setTimeout(resolve, nextDelay));
+
+      return poll();
+    }
+  };
+
+  return poll();
+}
+
+/**
+ * Result of license key activation
+ */
+export interface LicenseActivationResult {
+  success: boolean;
+  licenseType?: string;
+  licenseInfo?: LicenseInfo;
+  error?: string;
+}
+
+/**
+ * Activate a license key by saving it to the backend and fetching updated info
+ * Used for NEW subscriptions where we have a new license key to save
+ */
+export async function activateLicenseKey(
+  licenseKey: string,
+  options: {
+    /** Check if component is still mounted */
+    isMounted?: () => boolean;
+    /** Callback when license is activated with updated info */
+    onActivated?: (licenseInfo: LicenseInfo) => void;
+  } = {}
+): Promise<LicenseActivationResult> {
+  const { isMounted = () => true, onActivated } = options;
+
+  try {
+    console.log('Activating license key...');
+    const saveResponse = await licenseService.saveLicenseKey(licenseKey);
+
+    if (!isMounted()) {
+      return { success: false, error: 'Component unmounted' };
+    }
+
+    if (saveResponse.success) {
+      console.log(`License key activated: ${saveResponse.licenseType}`);
+
+      // Fetch updated license info
+      try {
+        const licenseInfo = await licenseService.getLicenseInfo();
+
+        if (!isMounted()) {
+          return { success: false, error: 'Component unmounted' };
+        }
+
+        onActivated?.(licenseInfo);
+
+        return {
+          success: true,
+          licenseType: saveResponse.licenseType,
+          licenseInfo,
+        };
+      } catch (infoError) {
+        console.error('Error fetching license info after activation:', infoError);
+        // Still return success since save succeeded
+        return {
+          success: true,
+          licenseType: saveResponse.licenseType,
+          error: 'Failed to fetch updated license info',
+        };
+      }
+    } else {
+      console.error('Failed to save license key:', saveResponse.error);
+      return {
+        success: false,
+        error: saveResponse.error || 'Failed to save license key',
+      };
+    }
+  } catch (error) {
+    console.error('Error activating license key:', error);
+    return {
+      success: false,
+      error: error instanceof Error ? error.message : 'Activation failed',
+    };
+  }
+}
+
+/**
+ * Resync existing license with Keygen
+ * Used for UPGRADES where we already have a license key configured
+ * Calls the dedicated resync endpoint instead of re-saving the same key
+ */
+export async function resyncExistingLicense(
+  options: {
+    /** Check if component is still mounted */
+    isMounted?: () => boolean;
+    /** Callback when license is resynced with updated info */
+    onActivated?: (licenseInfo: LicenseInfo) => void;
+  } = {}
+): Promise<LicenseActivationResult> {
+  const { isMounted = () => true, onActivated } = options;
+
+  try {
+    console.log('Resyncing existing license with Keygen...');
+    const resyncResponse = await licenseService.resyncLicense();
+
+    if (!isMounted()) {
+      return { success: false, error: 'Component unmounted' };
+    }
+
+    if (resyncResponse.success) {
+      console.log(`License resynced: ${resyncResponse.licenseType}`);
+
+      // Fetch updated license info
+      try {
+        const licenseInfo = await licenseService.getLicenseInfo();
+
+        if (!isMounted()) {
+          return { success: false, error: 'Component unmounted' };
+        }
+
+        onActivated?.(licenseInfo);
+
+        return {
+          success: true,
+          licenseType: resyncResponse.licenseType,
+          licenseInfo,
+        };
+      } catch (infoError) {
+        console.error('Error fetching license info after resync:', infoError);
+        // Still return success since resync succeeded
+        return {
+          success: true,
+          licenseType: resyncResponse.licenseType,
+          error: 'Failed to fetch updated license info',
+        };
+      }
+    } else {
+      console.error('Failed to resync license:', resyncResponse.error);
+      return {
+        success: false,
+        error: resyncResponse.error || 'Failed to resync license',
+      };
+    }
+  } catch (error) {
+    console.error('Error resyncing license:', error);
+    return {
+      success: false,
+      error: error instanceof Error ? error.message : 'Resync failed',
+    };
+  }
+}
diff --git a/frontend/src/proprietary/utils/protocolDetection.ts b/frontend/src/proprietary/utils/protocolDetection.ts
new file mode 100644
index 000000000..9bd9ce03b
--- /dev/null
+++ b/frontend/src/proprietary/utils/protocolDetection.ts
@@ -0,0 +1,43 @@
+/**
+ * Protocol detection utility for determining secure context
+ * Used to decide between Embedded Checkout (HTTPS) and Hosted Checkout (HTTP)
+ */
+
+/**
+ * Check if the current context is secure (HTTPS or localhost)
+ * @returns true if HTTPS or localhost, false if HTTP
+ */
+export function isSecureContext(): boolean {
+  // Allow localhost for development (works with both HTTP and HTTPS)
+  if (typeof window !== 'undefined') {
+    // const hostname = window.location.hostname;
+    const protocol = window.location.protocol;
+
+    // Localhost is considered secure for development
+    // if (hostname === 'localhost' || hostname === '127.0.0.1' || hostname === '[::1]') {
+    //   return true;
+    // }
+
+    // Check if HTTPS
+    return protocol === 'https:';
+  }
+
+  // Default to false if window is not available (SSR context)
+  return false;
+}
+
+/**
+ * Get the appropriate Stripe checkout UI mode based on current context
+ * @returns 'embedded' for HTTPS/localhost, 'hosted' for HTTP
+ */
+export function getCheckoutMode(): 'embedded' | 'hosted' {
+  return isSecureContext() ? 'embedded' : 'hosted';
+}
+
+/**
+ * Check if Embedded Checkout can be used in current context
+ * @returns true if secure context (HTTPS/localhost)
+ */
+export function canUseEmbeddedCheckout(): boolean {
+  return isSecureContext();
+}
diff --git a/frontend/tsconfig.desktop.json b/frontend/tsconfig.desktop.json
index fe0419a78..cb842c399 100644
--- a/frontend/tsconfig.desktop.json
+++ b/frontend/tsconfig.desktop.json
@@ -13,6 +13,10 @@
     }
   },
   "exclude": [
+    "src/core/**/*.test.ts*",
+    "src/core/**/*.spec.ts*",
+    "src/proprietary/**/*.test.ts*",
+    "src/proprietary/**/*.spec.ts*",
     "node_modules"
   ]
 }
diff --git a/frontend/tsconfig.proprietary.json b/frontend/tsconfig.proprietary.json
index 29f1b62df..4c726f09a 100644
--- a/frontend/tsconfig.proprietary.json
+++ b/frontend/tsconfig.proprietary.json
@@ -10,6 +10,8 @@
     }
   },
   "exclude": [
+    "src/core/**/*.test.ts*",
+    "src/core/**/*.spec.ts*",
     "src/desktop",
     "node_modules"
   ]
diff --git a/frontend/vite-env.d.ts b/frontend/vite-env.d.ts
index ca36e9027..f483e59d4 100644
--- a/frontend/vite-env.d.ts
+++ b/frontend/vite-env.d.ts
@@ -3,6 +3,8 @@
 interface ImportMetaEnv {
   readonly VITE_PUBLIC_POSTHOG_KEY: string;
   readonly VITE_PUBLIC_POSTHOG_HOST: string;
+  readonly VITE_SUPABASE_URL: string;
+  readonly VITE_SUPABASE_PUBLISHABLE_DEFAULT_KEY: string;
 }
 
 interface ImportMeta {
diff --git a/frontend/vite.config.ts b/frontend/vite.config.ts
index f7af0fdac..49aacd3ae 100644
--- a/frontend/vite.config.ts
+++ b/frontend/vite.config.ts
@@ -31,24 +31,25 @@ export default defineConfig(({ mode }) => {
         // tell vite to ignore watching `src-tauri`
         ignored: ['**/src-tauri/**'],
       },
-    proxy: {
-      '/api': {
-        target: 'http://localhost:8080',
-        changeOrigin: true,
-        secure: false,
-        xfwd: true,
-      },
-      '/oauth2': {
-        target: 'http://localhost:8080',
-        changeOrigin: true,
-        secure: false,
-        xfwd: true,
-      },
-      '/login/oauth2': {
-        target: 'http://localhost:8080',
-        changeOrigin: true,
-        secure: false,
-        xfwd: true,
+      // Only use proxy in web mode - Tauri handles backend connections directly
+      proxy: isDesktopMode ? undefined : {
+        '/api': {
+          target: 'http://localhost:8080',
+          changeOrigin: true,
+          secure: false,
+          xfwd: true,
+        },
+        '/oauth2': {
+          target: 'http://localhost:8080',
+          changeOrigin: true,
+          secure: false,
+          xfwd: true,
+        },
+        '/login/oauth2': {
+          target: 'http://localhost:8080',
+          changeOrigin: true,
+          secure: false,
+          xfwd: true,
         },
       },
     },
diff --git a/frontend/vitest.config.ts b/frontend/vitest.config.ts
index bf9880848..111099896 100644
--- a/frontend/vitest.config.ts
+++ b/frontend/vitest.config.ts
@@ -2,52 +2,87 @@ import { defineConfig } from 'vitest/config';
 import react from '@vitejs/plugin-react-swc';
 import tsconfigPaths from 'vite-tsconfig-paths';
 
-export default defineConfig((configEnv) => {
-  const isProprietary = process.env.DISABLE_ADDITIONAL_FEATURES !== 'true';
-  const isDesktopMode =
-    configEnv.mode === 'desktop' ||
-    process.env.STIRLING_DESKTOP === 'true' ||
-    process.env.VITE_DESKTOP === 'true';
-
-  const baseProject = isProprietary ? './tsconfig.proprietary.json' : './tsconfig.core.json';
-  const desktopProject = isProprietary ? './tsconfig.desktop.json' : baseProject;
-  const tsconfigProject = isDesktopMode ? desktopProject : baseProject;
-
-  return {
-    plugins: [
-      react(),
-      tsconfigPaths({
-        projects: [tsconfigProject],
-      }),
+export default defineConfig({
+  test: {
+    globals: true,
+    environment: 'jsdom',
+    setupFiles: ['./src/core/setupTests.ts'],
+    css: false,
+    exclude: [
+      'node_modules/',
+      'src/**/*.spec.ts', // Exclude Playwright E2E tests
+      'src/tests/test-fixtures/**'
     ],
-    test: {
-      globals: true,
-      environment: 'jsdom',
-      setupFiles: ['./src/core/setupTests.ts'],
-      css: false, // Disable CSS processing to speed up tests
-      include: [
-        'src/**/*.{test,spec}.{js,mjs,cjs,ts,mts,cts,jsx,tsx}'
-      ],
+    testTimeout: 10000,
+    hookTimeout: 10000,
+    coverage: {
+      reporter: ['text', 'json', 'html'],
       exclude: [
         'node_modules/',
-        'src/**/*.spec.ts', // Exclude Playwright E2E tests
-        'src/tests/test-fixtures/**'
-      ],
-      testTimeout: 10000, // 10 second timeout
-      hookTimeout: 10000, // 10 second timeout for setup/teardown
-      coverage: {
-        reporter: ['text', 'json', 'html'],
-        exclude: [
-          'node_modules/',
-          'src/core/setupTests.ts',
-          '**/*.d.ts',
-          'src/tests/test-fixtures/**',
-          'src/**/*.spec.ts' // Exclude Playwright files from coverage
-        ]
-      }
+        'src/core/setupTests.ts',
+        '**/*.d.ts',
+        'src/tests/test-fixtures/**',
+        'src/**/*.spec.ts'
+      ]
     },
-    esbuild: {
-      target: 'es2020' // Use older target to avoid warnings
-    }
-  };
+    projects: [
+      {
+        test: {
+          name: 'core',
+          include: ['src/core/**/*.test.{ts,tsx}'],
+          environment: 'jsdom',
+          globals: true,
+          setupFiles: ['./src/core/setupTests.ts'],
+        },
+        plugins: [
+          react(),
+          tsconfigPaths({
+            projects: ['./tsconfig.core.json'],
+          }),
+        ],
+        esbuild: {
+          target: 'es2020'
+        }
+      },
+      {
+        test: {
+          name: 'proprietary',
+          include: ['src/proprietary/**/*.test.{ts,tsx}'],
+          environment: 'jsdom',
+          globals: true,
+          setupFiles: ['./src/core/setupTests.ts'],
+        },
+        plugins: [
+          react(),
+          tsconfigPaths({
+            projects: ['./tsconfig.proprietary.json'],
+          }),
+        ],
+        esbuild: {
+          target: 'es2020'
+        }
+      },
+      {
+        test: {
+          name: 'desktop',
+          include: ['src/desktop/**/*.test.{ts,tsx}'],
+          environment: 'jsdom',
+          globals: true,
+          setupFiles: ['./src/core/setupTests.ts'],
+        },
+        plugins: [
+          react(),
+          tsconfigPaths({
+            projects: ['./tsconfig.desktop.json'],
+          }),
+        ],
+        esbuild: {
+          target: 'es2020'
+        }
+      },
+    ],
+  },
+  esbuild: {
+    target: 'es2020'
+  }
 });
diff --git a/scripts/ignore_translation.toml b/scripts/ignore_translation.toml
index 83e2df925..51565290f 100644
--- a/scripts/ignore_translation.toml
+++ b/scripts/ignore_translation.toml
@@ -50,7 +50,6 @@ ignore = [
 
 [ca_CA]
 ignore = [
-    'adminUserSettings.admin',
     'lang.amh',
     'lang.ceb',
     'lang.chr',
@@ -408,8 +407,6 @@ ignore = [
     'endpointStatistics.top20',
     'home.pipeline.title',
     'language.direction',
-    'pipeline.title',
-    'pipelineOptions.pipelineHeader',
     'pro',
     'showJS.tags',
 ]
@@ -612,7 +609,6 @@ ignore = [
     'lang.urd',
     'lang.yor',
     'language.direction',
-    'oops',
     'sponsor',
 ]
 
@@ -788,7 +784,6 @@ ignore = [
     'lang.urd',
     'lang.uzb',
     'language.direction',
-    'navbar.sections.security',
     'text',
     'watermark.type.1',
 ]
@@ -838,7 +833,6 @@ ignore = [
     'endpointStatistics.top10',
     'endpointStatistics.top20',
     'font',
-    'info',
     'lang.div',
     'lang.epo',
     'lang.hin',
@@ -896,7 +890,6 @@ ignore = [
     'lang.tir',
     'lang.uzb_cyrl',
     'language.direction',
-    'pipelineOptions.pipelineHeader',
     'showJS.tags',
 ]
 
@@ -987,6 +980,5 @@ ignore = [
 [zh_TW]
 ignore = [
     'language.direction',
-    'poweredBy',
     'showJS.tags',
 ]