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 9cb4a786a..de8d69797 100644
--- a/app/core/src/main/java/stirling/software/SPDF/SPDFApplication.java
+++ b/app/core/src/main/java/stirling/software/SPDF/SPDFApplication.java
@@ -141,10 +141,10 @@ public class SPDFApplication {
         String backendUrl = appConfig.getBackendUrl();
         String contextPath = appConfig.getContextPath();
         String serverPort = appConfig.getServerPort();
-        baseUrlStatic = backendUrl;
+        baseUrlStatic = normalizeBackendUrl(backendUrl, serverPort);
         contextPathStatic = contextPath;
         serverPortStatic = serverPort;
-        String url = backendUrl + ":" + getStaticPort() + contextPath;
+        String url = buildFullUrl(baseUrlStatic, getStaticPort(), contextPathStatic);
 
         // Log Tauri mode information
         if (Boolean.parseBoolean(System.getProperty("STIRLING_PDF_TAURI_MODE", "false"))) {
@@ -210,7 +210,7 @@ public class SPDFApplication {
 
     private static void printStartupLogs() {
         log.info("Stirling-PDF Started.");
-        String url = baseUrlStatic + ":" + getStaticPort() + contextPathStatic;
+        String url = buildFullUrl(baseUrlStatic, getStaticPort(), contextPathStatic);
         log.info("Navigate to {}", url);
     }
 
@@ -258,4 +258,40 @@ public class SPDFApplication {
     public static String getStaticContextPath() {
         return contextPathStatic;
     }
+
+    private static String buildFullUrl(String backendUrl, String port, String contextPath) {
+        String normalizedBase = normalizeBackendUrl(backendUrl, port);
+
+        String normalizedContextPath =
+                (contextPath == null || contextPath.isBlank() || "/".equals(contextPath))
+                        ? "/"
+                        : (contextPath.startsWith("/") ? contextPath : "/" + contextPath);
+
+        return normalizedBase + normalizedContextPath;
+    }
+
+    private static String normalizeBackendUrl(String backendUrl, String port) {
+        String trimmedBase =
+                (backendUrl == null || backendUrl.isBlank())
+                        ? "http://localhost"
+                        : backendUrl.trim().replaceAll("/+$", "");
+
+        try {
+            java.net.URI uri = new java.net.URI(trimmedBase);
+            boolean hasPort = uri.getPort() != -1;
+            boolean defaultHttp = "http".equalsIgnoreCase(uri.getScheme()) && "80".equals(port);
+            boolean defaultHttps = "https".equalsIgnoreCase(uri.getScheme()) && "443".equals(port);
+
+            if (hasPort || defaultHttp || defaultHttps) {
+                return trimmedBase;
+            }
+        } catch (java.net.URISyntaxException e) {
+            // If parsing fails, fall back to a simple suffix check
+            if (trimmedBase.matches(".+:\\d+$")) {
+                return trimmedBase;
+            }
+        }
+
+        return trimmedBase + ":" + port;
+    }
 }
diff --git a/app/core/src/main/java/stirling/software/SPDF/controller/web/ReactRoutingController.java b/app/core/src/main/java/stirling/software/SPDF/controller/web/ReactRoutingController.java
index eddff0e1e..20f004eea 100644
--- a/app/core/src/main/java/stirling/software/SPDF/controller/web/ReactRoutingController.java
+++ b/app/core/src/main/java/stirling/software/SPDF/controller/web/ReactRoutingController.java
@@ -19,20 +19,22 @@ import org.springframework.web.bind.annotation.GetMapping;
 import jakarta.annotation.PostConstruct;
 import jakarta.servlet.http.HttpServletRequest;
 
-import lombok.extern.slf4j.Slf4j;
-
 import stirling.software.common.configuration.InstallationPathConfig;
 
-@Slf4j
 @Controller
 public class ReactRoutingController {
 
+    private static final org.slf4j.Logger log =
+            org.slf4j.LoggerFactory.getLogger(ReactRoutingController.class);
+
     @Value("${server.servlet.context-path:/}")
     private String contextPath;
 
     private String cachedIndexHtml;
+    private String cachedCallbackHtml;
     private boolean indexHtmlExists = false;
     private boolean useExternalIndexHtml = false;
+    private boolean loggedMissingIndex = false;
 
     @PostConstruct
     public void init() {
@@ -43,56 +45,72 @@ public class ReactRoutingController {
         log.debug("Checking for custom index.html at: {}", externalIndexPath);
         if (Files.exists(externalIndexPath) && Files.isReadable(externalIndexPath)) {
             log.info("Using custom index.html from: {}", externalIndexPath);
-            try {
-                this.cachedIndexHtml = processIndexHtml();
-                this.indexHtmlExists = true;
-                this.useExternalIndexHtml = true;
-                return;
-            } catch (IOException e) {
-                log.warn("Failed to load custom index.html, falling back to classpath", e);
-            }
+            this.cachedIndexHtml = processIndexHtml();
+            this.indexHtmlExists = true;
+            this.useExternalIndexHtml = true;
+            return;
         }
 
         // Fall back to classpath index.html
         ClassPathResource resource = new ClassPathResource("static/index.html");
         if (resource.exists()) {
-            try {
-                this.cachedIndexHtml = processIndexHtml();
-                this.indexHtmlExists = true;
-                this.useExternalIndexHtml = false;
-            } catch (IOException e) {
-                // Failed to cache, will process on each request
-                log.warn("Failed to cache index.html", e);
-                this.indexHtmlExists = false;
+            this.cachedIndexHtml = processIndexHtml();
+            this.indexHtmlExists = true;
+            this.useExternalIndexHtml = false;
+            return;
+        }
+
+        // Neither external nor classpath index.html exists - cache fallback once
+        this.cachedIndexHtml = buildFallbackHtml();
+        this.cachedCallbackHtml = buildCallbackHtml();
+        this.indexHtmlExists = true;
+        this.useExternalIndexHtml = false;
+        this.loggedMissingIndex = true;
+        log.warn(
+                "index.html not found in classpath or custom path; using lightweight fallback page");
+    }
+
+    private String processIndexHtml() {
+        try {
+            Resource resource = getIndexHtmlResource();
+
+            if (!resource.exists()) {
+                if (!loggedMissingIndex) {
+                    log.warn("index.html not found, using lightweight fallback page");
+                    loggedMissingIndex = true;
+                }
+                return buildFallbackHtml();
             }
+
+            try (InputStream inputStream = resource.getInputStream()) {
+                String html = new String(inputStream.readAllBytes(), StandardCharsets.UTF_8);
+
+                // Replace %BASE_URL% with the actual context path for base href
+                String baseUrl = contextPath.endsWith("/") ? contextPath : contextPath + "/";
+                html = html.replace("%BASE_URL%", baseUrl);
+                // Also rewrite any existing <base> tag (Vite may have baked one in)
+                html =
+                        html.replaceFirst(
+                                "<base href=\\\"[^\\\"]*\\\"\\s*/?>",
+                                "<base href=\\\"" + baseUrl + "\\\" />");
+
+                // Inject context path as a global variable for API calls
+                String contextPathScript =
+                        "<script>window.STIRLING_PDF_API_BASE_URL = '" + baseUrl + "';</script>";
+                html = html.replace("</head>", contextPathScript + "</head>");
+
+                return html;
+            }
+        } catch (Exception ex) {
+            if (!loggedMissingIndex) {
+                log.warn("index.html not found, using lightweight fallback page", ex);
+                loggedMissingIndex = true;
+            }
+            return buildFallbackHtml();
         }
     }
 
-    private String processIndexHtml() throws IOException {
-        Resource resource = getIndexHtmlResource();
-
-        try (InputStream inputStream = resource.getInputStream()) {
-            String html = new String(inputStream.readAllBytes(), StandardCharsets.UTF_8);
-
-            // Replace %BASE_URL% with the actual context path for base href
-            String baseUrl = contextPath.endsWith("/") ? contextPath : contextPath + "/";
-            html = html.replace("%BASE_URL%", baseUrl);
-            // Also rewrite any existing <base> tag (Vite may have baked one in)
-            html =
-                    html.replaceFirst(
-                            "<base href=\\\"[^\\\"]*\\\"\\s*/?>",
-                            "<base href=\\\"" + baseUrl + "\\\" />");
-
-            // Inject context path as a global variable for API calls
-            String contextPathScript =
-                    "<script>window.STIRLING_PDF_API_BASE_URL = '" + baseUrl + "';</script>";
-            html = html.replace("</head>", contextPathScript + "</head>");
-
-            return html;
-        }
-    }
-
-    private Resource getIndexHtmlResource() throws IOException {
+    private Resource getIndexHtmlResource() {
         // Check external location first
         Path externalIndexPath = Paths.get(InstallationPathConfig.getStaticPath(), "index.html");
         if (Files.exists(externalIndexPath) && Files.isReadable(externalIndexPath)) {
@@ -106,12 +124,25 @@ public class ReactRoutingController {
     @GetMapping(
             value = {"/", "/index.html"},
             produces = MediaType.TEXT_HTML_VALUE)
-    public ResponseEntity<String> serveIndexHtml(HttpServletRequest request) throws IOException {
-        if (indexHtmlExists && cachedIndexHtml != null) {
-            return ResponseEntity.ok().contentType(MediaType.TEXT_HTML).body(cachedIndexHtml);
+    public ResponseEntity<String> serveIndexHtml(HttpServletRequest request) {
+        try {
+            if (indexHtmlExists && cachedIndexHtml != null) {
+                return ResponseEntity.ok().contentType(MediaType.TEXT_HTML).body(cachedIndexHtml);
+            }
+            // Fallback: process on each request (dev mode or cache failed)
+            return ResponseEntity.ok().contentType(MediaType.TEXT_HTML).body(processIndexHtml());
+        } catch (Exception ex) {
+            log.error("Failed to serve index.html, returning fallback", ex);
+            return ResponseEntity.ok().contentType(MediaType.TEXT_HTML).body(buildFallbackHtml());
         }
-        // Fallback: process on each request (dev mode or cache failed)
-        return ResponseEntity.ok().contentType(MediaType.TEXT_HTML).body(processIndexHtml());
+    }
+
+    @GetMapping(value = "/auth/callback", produces = MediaType.TEXT_HTML_VALUE)
+    public ResponseEntity<String> serveAuthCallback() {
+        if (cachedCallbackHtml == null) {
+            cachedCallbackHtml = buildCallbackHtml();
+        }
+        return ResponseEntity.ok().contentType(MediaType.TEXT_HTML).body(cachedCallbackHtml);
     }
 
     @GetMapping(
@@ -126,4 +157,104 @@ public class ReactRoutingController {
             throws IOException {
         return serveIndexHtml(request);
     }
+
+    private String buildFallbackHtml() {
+        String baseUrl = contextPath.endsWith("/") ? contextPath : contextPath + "/";
+        String serverUrl = "(window.location.origin + '" + baseUrl + "')";
+        return """
+                <!doctype html>
+                <html>
+                  <head>
+                    <meta charset="utf-8" />
+                    <base href="%s" />
+                    <title>Stirling PDF</title>
+                    <script>
+                      // Minimal handler for SSO callback when index.html is missing (desktop fallback)
+                      (function() {
+                        const baseUrl = '%s';
+                        window.STIRLING_PDF_API_BASE_URL = baseUrl;
+                        const hashParams = new URLSearchParams(window.location.hash.replace(/^#/, ''));
+                        const searchParams = new URLSearchParams(window.location.search);
+                        const token = hashParams.get('access_token') || hashParams.get('token') || searchParams.get('access_token');
+                        const isDesktopPopup = window.opener && window.name === 'stirling-desktop-sso';
+                        const serverUrl = %s;
+
+                        if (token) {
+                          try { localStorage.setItem('stirling_jwt', token); } catch (_) {}
+                          try { window.dispatchEvent(new Event('jwt-available')); } catch (_) {}
+
+                          if (isDesktopPopup) {
+                            try { window.opener.postMessage({ type: 'stirling-desktop-sso', token }, '*'); } catch (_) {}
+                            setTimeout(() => { try { window.close(); } catch (_) {} }, 150);
+                            return;
+                          }
+
+                          // Trigger deep link back to desktop app with token + server info
+                          try {
+                            const deepLink = `stirlingpdf://auth/sso-complete?server=${encodeURIComponent(serverUrl)}#access_token=${encodeURIComponent(token)}&type=sso-selfhosted`;
+                            window.location.href = deepLink;
+                            return;
+                          } catch (_) {
+                            // ignore deep link errors
+                          }
+                        }
+
+                        // No redirect to avoid loops when index.html is missing
+                      })();
+                    </script>
+                  </head>
+                  <body>
+                    <p>Stirling PDF is running.</p>
+                  </body>
+                </html>
+                """
+                .formatted(baseUrl, baseUrl, serverUrl);
+    }
+
+    private String buildCallbackHtml() {
+        String baseUrl = contextPath.endsWith("/") ? contextPath : contextPath + "/";
+        String serverUrl = "(window.location.origin + '" + baseUrl + "')";
+        return """
+                <!doctype html>
+                <html>
+                  <head>
+                    <meta charset="utf-8" />
+                    <base href="%s" />
+                    <title>Authentication Complete</title>
+                    <script>
+                      (function() {
+                        const hashParams = new URLSearchParams(window.location.hash.replace(/^#/, ''));
+                        const searchParams = new URLSearchParams(window.location.search);
+                        const token = hashParams.get('access_token') || hashParams.get('token') || searchParams.get('access_token');
+                        const isDesktopPopup = window.opener && window.name === 'stirling-desktop-sso';
+                        const serverUrl = %s;
+
+                        if (token) {
+                          try { localStorage.setItem('stirling_jwt', token); } catch (_) {}
+                          try { window.dispatchEvent(new Event('jwt-available')); } catch (_) {}
+
+                          if (isDesktopPopup) {
+                            try { window.opener.postMessage({ type: 'stirling-desktop-sso', token }, '*'); } catch (_) {}
+                            setTimeout(() => { try { window.close(); } catch (_) {} }, 150);
+                            return;
+                          }
+
+                          try {
+                            const deepLink = `stirlingpdf://auth/sso-complete?server=${encodeURIComponent(serverUrl)}#access_token=${encodeURIComponent(token)}&type=sso-selfhosted`;
+                            window.location.href = deepLink;
+                            return;
+                          } catch (_) {
+                            // ignore deep link errors
+                          }
+                        }
+                      })();
+                    </script>
+                  </head>
+                  <body>
+                    <p>Authentication complete. You can close this window.</p>
+                  </body>
+                </html>
+                """
+                .formatted(baseUrl, serverUrl);
+    }
 }
diff --git a/frontend/package-lock.json b/frontend/package-lock.json
index f788474bb..9ba5c8b72 100644
--- a/frontend/package-lock.json
+++ b/frontend/package-lock.json
@@ -49,6 +49,7 @@
         "@tauri-apps/api": "^2.5.0",
         "@tauri-apps/plugin-fs": "^2.4.0",
         "@tauri-apps/plugin-http": "^2.5.4",
+        "@tauri-apps/plugin-shell": "^2.3.3",
         "autoprefixer": "^10.4.21",
         "axios": "^1.12.2",
         "globals": "^16.4.0",
@@ -457,7 +458,6 @@
         }
       ],
       "license": "MIT",
-      "peer": true,
       "engines": {
         "node": ">=18"
       },
@@ -501,7 +501,6 @@
         }
       ],
       "license": "MIT",
-      "peer": true,
       "engines": {
         "node": ">=18"
       }
@@ -582,7 +581,6 @@
       "resolved": "https://registry.npmjs.org/@embedpdf/core/-/core-1.5.0.tgz",
       "integrity": "sha512-Yrh9XoVaT8cUgzgqpJ7hx5wg6BqQrCFirqqlSwVb+Ly9oNn4fZbR9GycIWmzJOU5XBnaOJjXfQSaDyoNP0woNA==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@embedpdf/engines": "1.5.0",
         "@embedpdf/models": "1.5.0"
@@ -682,7 +680,6 @@
       "resolved": "https://registry.npmjs.org/@embedpdf/plugin-history/-/plugin-history-1.5.0.tgz",
       "integrity": "sha512-p7PTNNaIr4gH3jLwX+eLJe1DeUXgi21kVGN6SRx/pocH8esg4jqoOeD/YiRRZoZnPOiy0jBXVhkPkwSmY7a2hQ==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@embedpdf/models": "1.5.0"
       },
@@ -699,7 +696,6 @@
       "resolved": "https://registry.npmjs.org/@embedpdf/plugin-interaction-manager/-/plugin-interaction-manager-1.5.0.tgz",
       "integrity": "sha512-ckHgTfvkW6c5Ta7Mc+Dl9C2foVnvEpqEJ84wyBnqrU0OWbe/jsiPhyKBVeartMGqNI/kVfaQTXupyrKhekAVmg==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@embedpdf/models": "1.5.0"
       },
@@ -717,7 +713,6 @@
       "resolved": "https://registry.npmjs.org/@embedpdf/plugin-loader/-/plugin-loader-1.5.0.tgz",
       "integrity": "sha512-P4YpIZfaW69etYIjphyaL4cGl2pB14h3OdTE0tRQ2pZYZHFLTvlt4q9B3PVSdhlSrHK5nob7jfLGon2U7xCslg==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@embedpdf/models": "1.5.0"
       },
@@ -771,7 +766,6 @@
       "resolved": "https://registry.npmjs.org/@embedpdf/plugin-render/-/plugin-render-1.5.0.tgz",
       "integrity": "sha512-ywwSj0ByrlkvrJIHKRzqxARkOZriki8VJUC+T4MV8fGyF4CzvCRJyKlPktahFz+VxhoodqTh7lBCib68dH+GvA==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@embedpdf/models": "1.5.0"
       },
@@ -806,7 +800,6 @@
       "resolved": "https://registry.npmjs.org/@embedpdf/plugin-scroll/-/plugin-scroll-1.5.0.tgz",
       "integrity": "sha512-RNmTZCZ8X1mA8cw9M7TMDuhO9GtkOalGha2bBL3En3D1IlDRS7PzNNMSMV7eqT7OQICSTltlpJ8p8Qi5esvL/Q==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@embedpdf/models": "1.5.0"
       },
@@ -843,7 +836,6 @@
       "resolved": "https://registry.npmjs.org/@embedpdf/plugin-selection/-/plugin-selection-1.5.0.tgz",
       "integrity": "sha512-zrxLBAZQoPswDuf9q9DrYaQc6B0Ysc2U1hueTjNH/4+ydfl0BFXZkKR63C2e3YmWtXvKjkoIj0GyPzsiBORLUw==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@embedpdf/models": "1.5.0"
       },
@@ -919,7 +911,6 @@
       "resolved": "https://registry.npmjs.org/@embedpdf/plugin-viewport/-/plugin-viewport-1.5.0.tgz",
       "integrity": "sha512-G8GDyYRhfehw72+r4qKkydnA5+AU8qH67g01Y12b0DzI0VIzymh/05Z4dK8DsY3jyWPXJfw2hlg5+KDHaMBHgQ==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@embedpdf/models": "1.5.0"
       },
@@ -1075,7 +1066,6 @@
       "resolved": "https://registry.npmjs.org/@emotion/react/-/react-11.14.0.tgz",
       "integrity": "sha512-O000MLDBDdk/EohJPFUqvnp4qnHeYkVP5B0xEG0D/L7cOKP9kefu2DXn8dj74cQfsEzUqh+sr1RzFqiL1o+PpA==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@babel/runtime": "^7.18.3",
         "@emotion/babel-plugin": "^11.13.5",
@@ -1119,7 +1109,6 @@
       "resolved": "https://registry.npmjs.org/@emotion/styled/-/styled-11.14.1.tgz",
       "integrity": "sha512-qEEJt42DuToa3gurlH4Qqc1kVpNq8wO8cJtDzU46TjlzWjDlsVyevtYCRijVq3SrHsROS+gVQ8Fnea108GnKzw==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@babel/runtime": "^7.18.3",
         "@emotion/babel-plugin": "^11.13.5",
@@ -2150,7 +2139,6 @@
       "resolved": "https://registry.npmjs.org/@mantine/core/-/core-8.3.6.tgz",
       "integrity": "sha512-paTl+0x+O/QtgMtqVJaG8maD8sfiOdgPmLOyG485FmeGZ1L3KMdEkhxZtmdGlDFsLXhmMGQ57ducT90bvhXX5A==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@floating-ui/react": "^0.27.16",
         "clsx": "^2.1.1",
@@ -2201,7 +2189,6 @@
       "resolved": "https://registry.npmjs.org/@mantine/hooks/-/hooks-8.3.6.tgz",
       "integrity": "sha512-liHfaWXHAkLjJy+Bkr29UsCwAoDQ/a64WrM67lksx8F0qqyjR5RQH8zVlhuOjdpQnwtlUkE/YiTvbJiPcoI0bw==",
       "license": "MIT",
-      "peer": true,
       "peerDependencies": {
         "react": "^18.x || ^19.x"
       }
@@ -2269,7 +2256,6 @@
       "resolved": "https://registry.npmjs.org/@mui/material/-/material-7.3.5.tgz",
       "integrity": "sha512-8VVxFmp1GIm9PpmnQoCoYo0UWHoOrdA57tDL62vkpzEgvb/d71Wsbv4FRg7r1Gyx7PuSo0tflH34cdl/NvfHNQ==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@babel/runtime": "^7.28.4",
         "@mui/core-downloads-tracker": "^7.3.5",
@@ -3202,7 +3188,6 @@
       "resolved": "https://registry.npmjs.org/@stripe/stripe-js/-/stripe-js-7.9.0.tgz",
       "integrity": "sha512-ggs5k+/0FUJcIgNY08aZTqpBTtbExkJMYMLSMwyucrhtWexVOEY1KJmhBsxf+E/Q15f5rbwBpj+t0t2AW2oCsQ==",
       "license": "MIT",
-      "peer": true,
       "engines": {
         "node": ">=12.16"
       }
@@ -3321,6 +3306,7 @@
       "resolved": "https://registry.npmjs.org/@sveltejs/acorn-typescript/-/acorn-typescript-1.0.6.tgz",
       "integrity": "sha512-4awhxtMh4cx9blePWl10HRHj8Iivtqj+2QdDCSMDzxG+XKa9+VCNupQuCuvzEhYPzZSrX+0gC+0lHA/0fFKKQQ==",
       "license": "MIT",
+      "peer": true,
       "peerDependencies": {
         "acorn": "^8.9.0"
       }
@@ -4091,13 +4077,21 @@
         "@tauri-apps/api": "^2.8.0"
       }
     },
+    "node_modules/@tauri-apps/plugin-shell": {
+      "version": "2.3.3",
+      "resolved": "https://registry.npmjs.org/@tauri-apps/plugin-shell/-/plugin-shell-2.3.3.tgz",
+      "integrity": "sha512-Xod+pRcFxmOWFWEnqH5yZcA7qwAMuaaDkMR1Sply+F8VfBj++CGnj2xf5UoialmjZ2Cvd8qrvSCbU+7GgNVsKQ==",
+      "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",
       "integrity": "sha512-o4PXJQidqJl82ckFaXUeoAW+XysPLauYI43Abki5hABd853iMhitooc6znOnczgbTYmEP6U6/y1ZyKAIsvMKGg==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@babel/code-frame": "^7.10.4",
         "@babel/runtime": "^7.12.5",
@@ -4426,7 +4420,6 @@
       "resolved": "https://registry.npmjs.org/@types/react/-/react-19.2.2.tgz",
       "integrity": "sha512-6mDvHUFSjyT2B2yeNx2nUgMxh9LtOWvkhIU3uePn2I2oyNymUAX1NIsdgviM4CH+JSrp2D2hsMvJOkxY+0wNRA==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "csstype": "^3.0.2"
       }
@@ -4437,7 +4430,6 @@
       "integrity": "sha512-9KQPoO6mZCi7jcIStSnlOWn2nEF3mNmyr3rIAsGnAbQKYbRLyqmeSc39EVgtxXVia+LMT8j3knZLAZAh+xLmrw==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "peerDependencies": {
         "@types/react": "^19.2.0"
       }
@@ -4507,7 +4499,6 @@
       "integrity": "sha512-6m1I5RmHBGTnUGS113G04DMu3CpSdxCAU/UvtjNWL4Nuf3MW9tQhiJqRlHzChIkhy6kZSAQmc+I1bcGjE3yNKg==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@typescript-eslint/scope-manager": "8.46.3",
         "@typescript-eslint/types": "8.46.3",
@@ -5221,6 +5212,7 @@
       "resolved": "https://registry.npmjs.org/@vue/reactivity/-/reactivity-3.5.24.tgz",
       "integrity": "sha512-BM8kBhtlkkbnyl4q+HiF5R5BL0ycDPfihowulm02q3WYp2vxgPcJuZO866qa/0u3idbMntKEtVNuAUp5bw4teg==",
       "license": "MIT",
+      "peer": true,
       "dependencies": {
         "@vue/shared": "3.5.24"
       }
@@ -5230,6 +5222,7 @@
       "resolved": "https://registry.npmjs.org/@vue/runtime-core/-/runtime-core-3.5.24.tgz",
       "integrity": "sha512-RYP/byyKDgNIqfX/gNb2PB55dJmM97jc9wyF3jK7QUInYKypK2exmZMNwnjueWwGceEkP6NChd3D2ZVEp9undQ==",
       "license": "MIT",
+      "peer": true,
       "dependencies": {
         "@vue/reactivity": "3.5.24",
         "@vue/shared": "3.5.24"
@@ -5240,6 +5233,7 @@
       "resolved": "https://registry.npmjs.org/@vue/runtime-dom/-/runtime-dom-3.5.24.tgz",
       "integrity": "sha512-Z8ANhr/i0XIluonHVjbUkjvn+CyrxbXRIxR7wn7+X7xlcb7dJsfITZbkVOeJZdP8VZwfrWRsWdShH6pngMxRjw==",
       "license": "MIT",
+      "peer": true,
       "dependencies": {
         "@vue/reactivity": "3.5.24",
         "@vue/runtime-core": "3.5.24",
@@ -5252,6 +5246,7 @@
       "resolved": "https://registry.npmjs.org/@vue/server-renderer/-/server-renderer-3.5.24.tgz",
       "integrity": "sha512-Yh2j2Y4G/0/4z/xJ1Bad4mxaAk++C2v4kaa8oSYTMJBJ00/ndPuxCnWeot0/7/qafQFLh5pr6xeV6SdMcE/G1w==",
       "license": "MIT",
+      "peer": true,
       "dependencies": {
         "@vue/compiler-ssr": "3.5.24",
         "@vue/shared": "3.5.24"
@@ -5278,7 +5273,6 @@
       "resolved": "https://registry.npmjs.org/acorn/-/acorn-8.15.0.tgz",
       "integrity": "sha512-NZyJarBfL7nWwIq+FDL6Zp/yHEhePMNnnJ0y3qfieCrmNvYct8uvtiV41UvlSe6apAfk0fY1FbWx+NwfmpvtTg==",
       "license": "MIT",
-      "peer": true,
       "bin": {
         "acorn": "bin/acorn"
       },
@@ -5686,6 +5680,7 @@
       "resolved": "https://registry.npmjs.org/axobject-query/-/axobject-query-4.1.0.tgz",
       "integrity": "sha512-qIj0G9wZbMGNLjLmg1PT6v2mE9AH2zlnADJD/2tC6E00hgmhUOfEB6greHPAfLRSufHqROIUTkw6E+M3lH0PTQ==",
       "license": "Apache-2.0",
+      "peer": true,
       "engines": {
         "node": ">= 0.4"
       }
@@ -5962,7 +5957,6 @@
         }
       ],
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "baseline-browser-mapping": "^2.8.19",
         "caniuse-lite": "^1.0.30001751",
@@ -7010,8 +7004,7 @@
       "resolved": "https://registry.npmjs.org/devtools-protocol/-/devtools-protocol-0.0.1521046.tgz",
       "integrity": "sha512-vhE6eymDQSKWUXwwA37NtTTVEzjtGVfDr3pRbsWEQ5onH/Snp2c+2xZHWJJawG/0hCCJLRGt4xVtEVUVILol4w==",
       "dev": true,
-      "license": "BSD-3-Clause",
-      "peer": true
+      "license": "BSD-3-Clause"
     },
     "node_modules/dezalgo": {
       "version": "1.0.4",
@@ -7406,7 +7399,6 @@
       "integrity": "sha512-BhHmn2yNOFA9H9JmmIVKJmd288g9hrVRDkdoIgRCRuSySRUHH7r/DI6aAXW9T1WwUuY3DFgrcaqB+deURBLR5g==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@eslint-community/eslint-utils": "^4.8.0",
         "@eslint-community/regexpp": "^4.12.1",
@@ -7577,7 +7569,6 @@
       "integrity": "sha512-whOE1HFo/qJDyX4SnXzP4N6zOWn79WhnCUY/iDR0mPfQZO8wcYE4JClzI2oZrhBnnMUCBCHZhO6VQyoBU95mZA==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@rtsao/scc": "^1.1.0",
         "array-includes": "^3.1.9",
@@ -7744,7 +7735,8 @@
       "version": "1.2.2",
       "resolved": "https://registry.npmjs.org/esm-env/-/esm-env-1.2.2.tgz",
       "integrity": "sha512-Epxrv+Nr/CaL4ZcFGPJIYLWFom+YeV1DqMLHJoEd9SYRxNbaFruBwfEX/kkHUJf55j2+TUbmDcmuilbP1TmXHA==",
-      "license": "MIT"
+      "license": "MIT",
+      "peer": true
     },
     "node_modules/espree": {
       "version": "10.4.0",
@@ -7809,6 +7801,7 @@
       "resolved": "https://registry.npmjs.org/esrap/-/esrap-2.1.2.tgz",
       "integrity": "sha512-DgvlIQeowRNyvLPWW4PT7Gu13WznY288Du086E751mwwbsgr29ytBiYeLzAGIo0qk3Ujob0SDk8TiSaM5WQzNg==",
       "license": "MIT",
+      "peer": true,
       "dependencies": {
         "@jridgewell/sourcemap-codec": "^1.4.15"
       }
@@ -8899,7 +8892,6 @@
         }
       ],
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@babel/runtime": "^7.27.6"
       },
@@ -9376,6 +9368,7 @@
       "resolved": "https://registry.npmjs.org/is-reference/-/is-reference-3.0.3.tgz",
       "integrity": "sha512-ixkJoqQvAP88E6wLydLGGqCJsrFUnqoH6HnaczB8XmDH1oaWU+xxdptvikTgaEhtZ53Ky6YXiBuUI2WXLMCwjw==",
       "license": "MIT",
+      "peer": true,
       "dependencies": {
         "@types/estree": "^1.0.6"
       }
@@ -9696,7 +9689,6 @@
       "integrity": "sha512-Pcfm3eZ+eO4JdZCXthW9tCDT3nF4K+9dmeZ+5X39n+Kqz0DDIABRP5CAEOHRFZk8RGuC2efksTJxrjp8EXCunQ==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@acemir/cssom": "^0.9.19",
         "@asamuzakjp/dom-selector": "^6.7.3",
@@ -10283,7 +10275,8 @@
       "version": "3.0.0",
       "resolved": "https://registry.npmjs.org/locate-character/-/locate-character-3.0.0.tgz",
       "integrity": "sha512-SW13ws7BjaeJ6p7Q6CO2nchbYEc3X3J6WrmTTDto7yMPqVSZTUyY5Tjbid+Ab8gLnATtygYtiDIJGQRRn2ZOiA==",
-      "license": "MIT"
+      "license": "MIT",
+      "peer": true
     },
     "node_modules/locate-path": {
       "version": "6.0.0",
@@ -11442,7 +11435,6 @@
         }
       ],
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "nanoid": "^3.3.11",
         "picocolors": "^1.1.1",
@@ -11722,7 +11714,6 @@
       "resolved": "https://registry.npmjs.org/preact/-/preact-10.27.2.tgz",
       "integrity": "sha512-5SYSgFKSyhCbk6SrXyMpqjb5+MQBgfvEKE/OC+PujcY34sOpqtr+0AZQtPYx5IA6VxynQ7rUPCtKzyovpj9Bpg==",
       "license": "MIT",
-      "peer": true,
       "funding": {
         "type": "opencollective",
         "url": "https://opencollective.com/preact"
@@ -12105,7 +12096,6 @@
       "resolved": "https://registry.npmjs.org/react/-/react-19.2.0.tgz",
       "integrity": "sha512-tmbWg6W31tQLeB5cdIBOicJDJRR2KzXsV7uSK9iNfLWQ5bIZfxuPEHp7M8wiHyHnn0DD1i7w3Zmin0FtkrwoCQ==",
       "license": "MIT",
-      "peer": true,
       "engines": {
         "node": ">=0.10.0"
       }
@@ -12115,7 +12105,6 @@
       "resolved": "https://registry.npmjs.org/react-dom/-/react-dom-19.2.0.tgz",
       "integrity": "sha512-UlbRu4cAiGaIewkPyiRGJk0imDN2T3JjieT6spoL2UeSf5od4n5LB/mQ4ejmxhCFT1tYe8IvaFulzynWovsEFQ==",
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "scheduler": "^0.27.0"
       },
@@ -13627,6 +13616,7 @@
       "resolved": "https://registry.npmjs.org/aria-query/-/aria-query-5.3.2.tgz",
       "integrity": "sha512-COROpnaoap1E2F000S62r6A60uHZnmlvomhfyT2DlTcrY1OrBKn2UhH7qn5wTC9zMvD0AY7csdPSNwKP+7WiQw==",
       "license": "Apache-2.0",
+      "peer": true,
       "engines": {
         "node": ">= 0.4"
       }
@@ -13835,7 +13825,6 @@
       "integrity": "sha512-5gTmgEY/sqK6gFXLIsQNH19lWb4ebPDLA4SdLP7dsWkIXHWlG66oPuVvXSGFPppYZz8ZDZq0dYYrbHfBCVUb1Q==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "engines": {
         "node": ">=12"
       },
@@ -14137,7 +14126,6 @@
       "integrity": "sha512-jl1vZzPDinLr9eUt3J/t7V6FgNEw9QjvBPdysz9KfQDD41fQrC2Y4vKQdiaUpFT4bXlb1RHhLpp8wtm6M5TgSw==",
       "devOptional": true,
       "license": "Apache-2.0",
-      "peer": true,
       "bin": {
         "tsc": "bin/tsc",
         "tsserver": "bin/tsserver"
@@ -14219,7 +14207,6 @@
       "dev": true,
       "hasInstallScript": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "napi-postinstall": "^0.3.0"
       },
@@ -14424,7 +14411,6 @@
       "integrity": "sha512-BxAKBWmIbrDgrokdGZH1IgkIk/5mMHDreLDmCJ0qpyJaAteP8NvMhkwr/ZCQNqNH97bw/dANTE9PDzqwJghfMQ==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "esbuild": "^0.25.0",
         "fdir": "^6.5.0",
@@ -14595,7 +14581,6 @@
       "integrity": "sha512-5gTmgEY/sqK6gFXLIsQNH19lWb4ebPDLA4SdLP7dsWkIXHWlG66oPuVvXSGFPppYZz8ZDZq0dYYrbHfBCVUb1Q==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "engines": {
         "node": ">=12"
       },
@@ -14609,7 +14594,6 @@
       "integrity": "sha512-LUCP5ev3GURDysTWiP47wRRUpLKMOfPh+yKTx3kVIEiu5KOMeqzpnYNsKyOoVrULivR8tLcks4+lga33Whn90A==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@types/chai": "^5.2.2",
         "@vitest/expect": "3.2.4",
@@ -15221,7 +15205,8 @@
       "version": "1.1.4",
       "resolved": "https://registry.npmjs.org/zimmerframe/-/zimmerframe-1.1.4.tgz",
       "integrity": "sha512-B58NGBEoc8Y9MWWCQGl/gq9xBCe4IiKM0a2x7GZdQKOW5Exr8S1W24J6OgM1njK8xCRGvAJIL/MxXHf6SkmQKQ==",
-      "license": "MIT"
+      "license": "MIT",
+      "peer": true
     },
     "node_modules/zod": {
       "version": "3.25.76",
diff --git a/frontend/package.json b/frontend/package.json
index 914b7bb1f..e94494198 100644
--- a/frontend/package.json
+++ b/frontend/package.json
@@ -45,6 +45,7 @@
     "@tauri-apps/api": "^2.5.0",
     "@tauri-apps/plugin-fs": "^2.4.0",
     "@tauri-apps/plugin-http": "^2.5.4",
+    "@tauri-apps/plugin-shell": "^2.3.3",
     "autoprefixer": "^10.4.21",
     "axios": "^1.12.2",
     "globals": "^16.4.0",
diff --git a/frontend/src/desktop/components/SetupWizard/DesktopOAuthButtons.tsx b/frontend/src/desktop/components/SetupWizard/DesktopOAuthButtons.tsx
index 49b55a386..97761783b 100644
--- a/frontend/src/desktop/components/SetupWizard/DesktopOAuthButtons.tsx
+++ b/frontend/src/desktop/components/SetupWizard/DesktopOAuthButtons.tsx
@@ -3,16 +3,24 @@ import { useTranslation } from 'react-i18next';
 import { authService, UserInfo } from '@app/services/authService';
 import { buildOAuthCallbackHtml } from '@app/utils/oauthCallbackHtml';
 import { BASE_PATH } from '@app/constants/app';
+import { STIRLING_SAAS_URL } from '@desktop/constants/connection';
 import '@app/routes/authShared/auth.css';
 
-export type OAuthProvider = 'google' | 'github' | 'keycloak' | 'azure' | 'apple' | 'oidc';
+export type OAuthProviderId = 'google' | 'github' | 'keycloak' | 'azure' | 'apple' | 'oidc' | string;
+
+export interface DesktopSSOProvider {
+  id: OAuthProviderId;
+  path?: string;
+  label?: string;
+}
 
 interface DesktopOAuthButtonsProps {
   onOAuthSuccess: (userInfo: UserInfo) => Promise<void>;
   onError: (error: string) => void;
   isDisabled: boolean;
   serverUrl: string;
-  providers: OAuthProvider[];
+  providers: DesktopSSOProvider[];
+  mode?: 'saas' | 'selfHosted';
 }
 
 export const DesktopOAuthButtons: React.FC<DesktopOAuthButtonsProps> = ({
@@ -21,11 +29,12 @@ export const DesktopOAuthButtons: React.FC<DesktopOAuthButtonsProps> = ({
   isDisabled,
   serverUrl,
   providers,
+  mode = 'saas',
 }) => {
   const { t } = useTranslation();
   const [oauthLoading, setOauthLoading] = useState(false);
 
-  const handleOAuthLogin = async (provider: OAuthProvider) => {
+  const handleOAuthLogin = async (provider: DesktopSSOProvider) => {
     // Prevent concurrent OAuth attempts
     if (oauthLoading || isDisabled) {
       return;
@@ -48,7 +57,12 @@ export const DesktopOAuthButtons: React.FC<DesktopOAuthButtonsProps> = ({
         errorPlaceholder: true, // {error} will be replaced by Rust
       });
 
-      const userInfo = await authService.loginWithOAuth(provider, serverUrl, successHtml, errorHtml);
+      const normalizedServer = serverUrl.replace(/\/+$/, '');
+      const usingSupabaseFlow =
+        mode === 'saas' || normalizedServer === STIRLING_SAAS_URL.replace(/\/+$/, '');
+      const userInfo = usingSupabaseFlow
+        ? await authService.loginWithOAuth(provider.id, serverUrl, successHtml, errorHtml)
+        : await authService.loginWithSelfHostedOAuth(provider.path || provider.id, serverUrl);
 
       // Call the onOAuthSuccess callback to complete setup
       await onOAuthSuccess(userInfo);
@@ -64,7 +78,7 @@ export const DesktopOAuthButtons: React.FC<DesktopOAuthButtonsProps> = ({
     }
   };
 
-  const providerConfig: Record<OAuthProvider, { label: string; file: string }> = {
+  const providerConfig: Record<string, { label: string; file: string }> = {
     google: { label: 'Google', file: 'google.svg' },
     github: { label: 'GitHub', file: 'github.svg' },
     keycloak: { label: 'Keycloak', file: 'keycloak.svg' },
@@ -72,6 +86,7 @@ export const DesktopOAuthButtons: React.FC<DesktopOAuthButtonsProps> = ({
     apple: { label: 'Apple', file: 'apple.svg' },
     oidc: { label: 'OpenID', file: 'oidc.svg' },
   };
+  const GENERIC_PROVIDER_ICON = 'oidc.svg';
 
   if (providers.length === 0) {
     return null;
@@ -80,23 +95,29 @@ export const DesktopOAuthButtons: React.FC<DesktopOAuthButtonsProps> = ({
   return (
     <div className="oauth-container-vertical">
       {providers
-        .filter((providerId) => providerId in providerConfig)
-        .map((providerId) => {
-          const provider = providerConfig[providerId];
+        .filter((providerConfigEntry) => providerConfigEntry && providerConfigEntry.id)
+        .map((providerEntry) => {
+          const iconConfig = providerConfig[providerEntry.id];
+          const label =
+            providerEntry.label ||
+            iconConfig?.label ||
+            (providerEntry.id
+              ? providerEntry.id.charAt(0).toUpperCase() + providerEntry.id.slice(1)
+              : t('setup.login.sso', 'Single Sign-On'));
           return (
             <button
-              key={providerId}
-              onClick={() => handleOAuthLogin(providerId)}
+              key={providerEntry.id}
+              onClick={() => handleOAuthLogin(providerEntry)}
               disabled={isDisabled || oauthLoading}
               className="oauth-button-vertical"
-              title={provider.label}
+              title={label}
             >
               <img
-                src={`${BASE_PATH}/Login/${provider.file}`}
-                alt={provider.label}
+                src={`${BASE_PATH}/Login/${iconConfig?.file || GENERIC_PROVIDER_ICON}`}
+                alt={label}
                 className="oauth-icon-tiny"
               />
-              {provider.label}
+              {label}
             </button>
           );
         })}
diff --git a/frontend/src/desktop/components/SetupWizard/SaaSLoginScreen.tsx b/frontend/src/desktop/components/SetupWizard/SaaSLoginScreen.tsx
index 6acd28858..644e5fa98 100644
--- a/frontend/src/desktop/components/SetupWizard/SaaSLoginScreen.tsx
+++ b/frontend/src/desktop/components/SetupWizard/SaaSLoginScreen.tsx
@@ -66,7 +66,11 @@ export const SaaSLoginScreen: React.FC<SaaSLoginScreenProps> = ({
         onError={handleOAuthError}
         isDisabled={loading}
         serverUrl={serverUrl}
-        providers={['google', 'github']}
+        mode="saas"
+        providers={[
+          { id: 'google' },
+          { id: 'github' },
+        ]}
       />
 
       <DividerWithText
diff --git a/frontend/src/desktop/components/SetupWizard/SelfHostedLoginScreen.tsx b/frontend/src/desktop/components/SetupWizard/SelfHostedLoginScreen.tsx
index 9a68b9156..f90684518 100644
--- a/frontend/src/desktop/components/SetupWizard/SelfHostedLoginScreen.tsx
+++ b/frontend/src/desktop/components/SetupWizard/SelfHostedLoginScreen.tsx
@@ -5,13 +5,14 @@ import LoginHeader from '@app/routes/login/LoginHeader';
 import ErrorMessage from '@app/routes/login/ErrorMessage';
 import EmailPasswordForm from '@app/routes/login/EmailPasswordForm';
 import DividerWithText from '@app/components/shared/DividerWithText';
-import { DesktopOAuthButtons, OAuthProvider } from '@app/components/SetupWizard/DesktopOAuthButtons';
+import { DesktopOAuthButtons } from '@app/components/SetupWizard/DesktopOAuthButtons';
 import { UserInfo } from '@app/services/authService';
+import { SSOProviderConfig } from '@app/services/connectionModeService';
 import '@app/routes/authShared/auth.css';
 
 interface SelfHostedLoginScreenProps {
   serverUrl: string;
-  enabledOAuthProviders?: string[];
+  enabledOAuthProviders?: SSOProviderConfig[];
   onLogin: (username: string, password: string) => Promise<void>;
   onOAuthSuccess: (userInfo: UserInfo) => Promise<void>;
   loading: boolean;
@@ -74,7 +75,8 @@ export const SelfHostedLoginScreen: React.FC<SelfHostedLoginScreenProps> = ({
             onError={handleOAuthError}
             isDisabled={loading}
             serverUrl={serverUrl}
-            providers={enabledOAuthProviders as OAuthProvider[]}
+            mode="selfHosted"
+            providers={enabledOAuthProviders}
           />
 
           <DividerWithText
diff --git a/frontend/src/desktop/components/SetupWizard/ServerSelection.tsx b/frontend/src/desktop/components/SetupWizard/ServerSelection.tsx
index f8a0d4f9e..c463ab9a4 100644
--- a/frontend/src/desktop/components/SetupWizard/ServerSelection.tsx
+++ b/frontend/src/desktop/components/SetupWizard/ServerSelection.tsx
@@ -1,7 +1,7 @@
 import React, { useState } from 'react';
 import { Stack, Button, TextInput, Alert, Text } from '@mantine/core';
 import { useTranslation } from 'react-i18next';
-import { ServerConfig } from '@app/services/connectionModeService';
+import { ServerConfig, SSOProviderConfig } from '@app/services/connectionModeService';
 import { connectionModeService } from '@app/services/connectionModeService';
 import LocalIcon from '@app/components/shared/LocalIcon';
 
@@ -43,7 +43,7 @@ export const ServerSelection: React.FC<ServerSelectionProps> = ({ onSelect, load
       }
 
       // Fetch OAuth providers and check if login is enabled
-      let enabledProviders: string[] = [];
+      const enabledProviders: SSOProviderConfig[] = [];
       try {
         const response = await fetch(`${url}/api/v1/proprietary/ui-data/login`);
 
@@ -76,9 +76,19 @@ export const ServerSelection: React.FC<ServerSelectionProps> = ({ onSelect, load
 
         // Extract provider IDs from authorization URLs
         // Example: "/oauth2/authorization/google" → "google"
-        enabledProviders = Object.keys(data.providerList || {})
-          .map(key => key.split('/').pop())
-          .filter((id): id is string => id !== undefined);
+        const providerEntries = Object.entries(data.providerList || {});
+        providerEntries.forEach(([path, label]) => {
+          const id = path.split('/').pop();
+          if (!id) {
+            return;
+          }
+
+          enabledProviders.push({
+            id,
+            path,
+            label: typeof label === 'string' ? label : undefined,
+          });
+        });
 
         console.log('[ServerSelection] Detected OAuth providers:', enabledProviders);
       } catch (err) {
diff --git a/frontend/src/desktop/components/SetupWizard/index.tsx b/frontend/src/desktop/components/SetupWizard/index.tsx
index 9fbd0e6cc..b6e18a6c7 100644
--- a/frontend/src/desktop/components/SetupWizard/index.tsx
+++ b/frontend/src/desktop/components/SetupWizard/index.tsx
@@ -155,6 +155,28 @@ export const SetupWizard: React.FC<SetupWizardProps> = ({ onComplete }) => {
         const params = new URLSearchParams(hash);
         const accessToken = params.get('access_token');
         const type = params.get('type') || parsed.searchParams.get('type');
+        const accessTokenFromHash = params.get('access_token');
+        const accessTokenFromQuery = parsed.searchParams.get('access_token');
+        const serverFromQuery = parsed.searchParams.get('server');
+
+        // Handle self-hosted SSO deep link
+        if (type === 'sso' || type === 'sso-selfhosted') {
+          const token = accessTokenFromHash || accessTokenFromQuery;
+          const serverUrl = serverFromQuery || serverConfig?.url || STIRLING_SAAS_URL;
+          if (!token || !serverUrl) {
+            console.error('[SetupWizard] Deep link missing token or server for SSO completion');
+            return;
+          }
+
+          setLoading(true);
+          setError(null);
+
+          await authService.completeSelfHostedSession(serverUrl, token);
+          await connectionModeService.switchToSelfHosted({ url: serverUrl });
+          await tauriBackendService.initializeExternalBackend();
+          onComplete();
+          return;
+        }
 
         if (!type || (type !== 'signup' && type !== 'recovery' && type !== 'magiclink')) {
           return;
diff --git a/frontend/src/desktop/services/authService.ts b/frontend/src/desktop/services/authService.ts
index 710518f36..11d408e61 100644
--- a/frontend/src/desktop/services/authService.ts
+++ b/frontend/src/desktop/services/authService.ts
@@ -1,4 +1,6 @@
-import { invoke } from '@tauri-apps/api/core';
+import { invoke, isTauri } from '@tauri-apps/api/core';
+import { listen } from '@tauri-apps/api/event';
+import { open as shellOpen } from '@tauri-apps/plugin-shell';
 import axios from 'axios';
 import { DESKTOP_DEEP_LINK_CALLBACK, STIRLING_SAAS_URL, SUPABASE_KEY } from '@app/constants/connection';
 
@@ -436,6 +438,250 @@ export class AuthService {
     }
   }
 
+  /**
+   * Self-hosted SSO/OAuth2 flow for the desktop app.
+   * Opens a popup to the server's auth endpoint and listens for the AuthCallback page
+   * to postMessage the JWT back to the main window.
+   */
+  async loginWithSelfHostedOAuth(providerPath: string, serverUrl: string): Promise<UserInfo> {
+    const trimmedServer = serverUrl.replace(/\/+$/, '');
+    const fullUrl = providerPath.startsWith('http')
+      ? providerPath
+      : `${trimmedServer}${providerPath.startsWith('/') ? providerPath : `/${providerPath}`}`;
+
+    // Ensure backend redirects back to /auth/callback
+    try {
+      document.cookie = `stirling_redirect_path=${encodeURIComponent('/auth/callback')}; path=/; max-age=300; SameSite=Lax`;
+    } catch {
+      // ignore cookie errors
+    }
+
+    // Force a real popup so the main webview stays on the app
+    const authWindow = window.open(fullUrl, '_blank', 'width=900,height=900');
+
+    // Fallback: use Tauri shell.open and wait for deep link back
+    if (!authWindow) {
+      if (await this.openInSystemBrowser(fullUrl)) {
+        return this.waitForDeepLinkCompletion(trimmedServer);
+      }
+      throw new Error('Unable to open browser window for SSO. Please allow pop-ups and try again.');
+    }
+
+    const expectedOrigin = new URL(fullUrl).origin;
+
+    // Always also listen for deep link completion in case the opener messaging path fails
+    const deepLinkPromise = this.waitForDeepLinkCompletion(trimmedServer).catch(() => null);
+
+    return new Promise<UserInfo>((resolve, reject) => {
+      let completed = false;
+
+      const cleanup = () => {
+        window.removeEventListener('message', handleMessage);
+        clearInterval(windowCheck);
+        clearInterval(localTokenCheck);
+        clearTimeout(timeoutId);
+      };
+
+      const handleMessage = async (event: MessageEvent) => {
+        if (event.origin !== expectedOrigin) {
+          return;
+        }
+
+        const data = event.data as { type?: string; token?: string; access_token?: string };
+        if (!data || data.type !== 'stirling-desktop-sso') {
+          return;
+        }
+
+        const token = data.token || data.access_token;
+        if (!token) {
+          cleanup();
+          reject(new Error('No token returned from SSO'));
+          return;
+        }
+
+        completed = true;
+        cleanup();
+
+        try {
+          const userInfo = await this.completeSelfHostedSession(trimmedServer, token);
+          try {
+            authWindow.close();
+          } catch (closeError) {
+            console.warn('Could not close auth window:', closeError);
+          }
+          resolve(userInfo);
+        } catch (err) {
+          reject(err instanceof Error ? err : new Error('Failed to complete login'));
+        }
+      };
+
+      // If deep link finishes first, resolve
+      deepLinkPromise.then(async (dlResult) => {
+        if (completed || !dlResult) return;
+        completed = true;
+        cleanup();
+        resolve(dlResult);
+      }).catch(() => {
+        // ignore deep link errors here
+      });
+
+      window.addEventListener('message', handleMessage);
+
+      const windowCheck = window.setInterval(() => {
+        if (authWindow.closed && !completed) {
+          cleanup();
+          reject(new Error('Authentication window was closed before completion'));
+        }
+      }, 500);
+
+      const localTokenCheck = window.setInterval(async () => {
+        if (completed) {
+          clearInterval(localTokenCheck);
+          return;
+        }
+        const token = localStorage.getItem('stirling_jwt');
+        if (token) {
+          completed = true;
+          cleanup();
+          try {
+            const userInfo = await this.completeSelfHostedSession(trimmedServer, token);
+            try {
+              authWindow.close();
+            } catch (_) {
+              // ignore close errors
+            }
+            resolve(userInfo);
+          } catch (err) {
+            reject(err instanceof Error ? err : new Error('Failed to complete login'));
+          }
+        }
+      }, 1000);
+
+      const timeoutId = window.setTimeout(() => {
+        if (!completed) {
+          cleanup();
+          try {
+            authWindow.close();
+          } catch {
+            // ignore close errors
+          }
+          reject(new Error('SSO login timed out. Please try again.'));
+        }
+      }, 120_000);
+    });
+  }
+
+  /**
+   * Wait for a deep-link event to complete self-hosted SSO (used when popup cannot open)
+   */
+  private async waitForDeepLinkCompletion(serverUrl: string): Promise<UserInfo> {
+    if (!isTauri()) {
+      throw new Error('Unable to open browser window for SSO. Please allow pop-ups and try again.');
+    }
+
+    return new Promise<UserInfo>((resolve, reject) => {
+      let completed = false;
+      let unlisten: (() => void) | null = null;
+
+      const timeoutId = window.setTimeout(() => {
+        if (!completed) {
+          if (unlisten) unlisten();
+          reject(new Error('SSO login timed out. Please try again.'));
+        }
+      }, 120_000);
+
+      listen<string>('deep-link', async (event) => {
+        const url = event.payload;
+        if (!url || completed) return;
+        try {
+          const parsed = new URL(url);
+          const hash = parsed.hash.replace(/^#/, '');
+          const params = new URLSearchParams(hash);
+          const type = params.get('type') || parsed.searchParams.get('type');
+          if (type !== 'sso' && type !== 'sso-selfhosted') {
+            return;
+          }
+          const token = params.get('access_token') || parsed.searchParams.get('access_token');
+          if (!token) {
+            return;
+          }
+
+          completed = true;
+          if (unlisten) unlisten();
+          clearTimeout(timeoutId);
+
+          const userInfo = await this.completeSelfHostedSession(serverUrl, token);
+          resolve(userInfo);
+        } catch (err) {
+          completed = true;
+          if (unlisten) unlisten();
+          clearTimeout(timeoutId);
+          reject(err instanceof Error ? err : new Error('Failed to complete SSO'));
+        }
+      }).then((fn) => {
+        unlisten = fn;
+      });
+    });
+  }
+
+  private async openInSystemBrowser(url: string): Promise<boolean> {
+    if (!isTauri()) {
+      return false;
+    }
+    try {
+      // Prefer plugin-shell (2.x) if available
+      await shellOpen(url);
+      return true;
+    } catch (err) {
+      console.error('Failed to open system browser for SSO:', err);
+      return false;
+    }
+  }
+
+  /**
+   * Save JWT + user info for self-hosted SSO logins
+   */
+  async completeSelfHostedSession(serverUrl: string, token: string): Promise<UserInfo> {
+    await this.saveTokenEverywhere(token);
+
+    const userInfo = await this.fetchSelfHostedUserInfo(serverUrl, token);
+
+    await invoke('save_user_info', {
+      username: userInfo.username,
+      email: userInfo.email || null,
+    });
+
+    this.setAuthStatus('authenticated', userInfo);
+    return userInfo;
+  }
+
+  private async fetchSelfHostedUserInfo(serverUrl: string, token: string): Promise<UserInfo> {
+    try {
+      const response = await axios.get(
+        `${serverUrl.replace(/\/+$/, '')}/api/v1/auth/me`,
+        {
+          headers: {
+            Authorization: `Bearer ${token}`,
+          },
+        }
+      );
+
+      const data = response.data;
+      const user = data.user || data;
+
+      return {
+        username: user.username || user.email || 'User',
+        email: user.email || undefined,
+      };
+    } catch (error) {
+      console.error('[Desktop AuthService] Failed to fetch user info after SSO:', error);
+      return {
+        username: 'User',
+        email: undefined,
+      };
+    }
+  }
+
   /**
    * Fetch user info from Supabase using access token
    */
diff --git a/frontend/src/desktop/services/connectionModeService.ts b/frontend/src/desktop/services/connectionModeService.ts
index cf454a50b..c4db4d641 100644
--- a/frontend/src/desktop/services/connectionModeService.ts
+++ b/frontend/src/desktop/services/connectionModeService.ts
@@ -3,9 +3,15 @@ import { fetch } from '@tauri-apps/plugin-http';
 
 export type ConnectionMode = 'saas' | 'selfhosted';
 
+export interface SSOProviderConfig {
+  id: string;
+  path: string;
+  label?: string;
+}
+
 export interface ServerConfig {
   url: string;
-  enabledOAuthProviders?: string[];
+  enabledOAuthProviders?: SSOProviderConfig[];
 }
 
 export interface ConnectionConfig {
diff --git a/frontend/src/proprietary/routes/AuthCallback.tsx b/frontend/src/proprietary/routes/AuthCallback.tsx
index 488a54146..676c4f0e4 100644
--- a/frontend/src/proprietary/routes/AuthCallback.tsx
+++ b/frontend/src/proprietary/routes/AuthCallback.tsx
@@ -1,6 +1,8 @@
 import { useEffect } from 'react';
 import { useNavigate } from 'react-router-dom';
 import { springAuth } from '@app/auth/springAuthClient';
+import { connectionModeService } from '@app/services/connectionModeService';
+import { tauriBackendService } from '@app/services/tauriBackendService';
 
 /**
  * OAuth Callback Handler
@@ -52,6 +54,44 @@ export default function AuthCallback() {
           return;
         }
 
+        // Notify desktop popup listeners (self-hosted SSO flow)
+        const isDesktopPopup = typeof window !== 'undefined' && window.opener && window.name === 'stirling-desktop-sso';
+        if (isDesktopPopup) {
+          try {
+            window.opener.postMessage(
+              { type: 'stirling-desktop-sso', token },
+              '*'
+            );
+          } catch (postError) {
+            console.error('[AuthCallback] Failed to notify desktop window:', postError);
+          }
+
+          // Give the message a moment to flush before attempting to close
+          setTimeout(() => {
+            try {
+              window.close();
+            } catch (_) {
+              // ignore close errors
+            }
+          }, 150);
+        }
+
+        // Desktop fallback flow (when popup was blocked and we navigated directly)
+        try {
+          const pending = localStorage.getItem('desktop_self_hosted_sso_pending');
+          const hasTauri = typeof window !== 'undefined' && (window as any).__TAURI_INTERNALS__;
+          if (pending && hasTauri) {
+            const parsed = JSON.parse(pending) as { serverUrl?: string } | null;
+            if (parsed?.serverUrl) {
+              await connectionModeService.switchToSelfHosted({ url: parsed.serverUrl });
+              await tauriBackendService.initializeExternalBackend();
+            }
+            localStorage.removeItem('desktop_self_hosted_sso_pending');
+          }
+        } catch (desktopError) {
+          console.error('[AuthCallback] Desktop fallback completion failed:', desktopError);
+        }
+
         console.log('[AuthCallback] Token validated, redirecting to home');
 
         // Clear the hash from URL and redirect to home page