diff --git a/client/pages/upload/index.vue b/client/pages/upload/index.vue
index eef05b60..3216838f 100644
--- a/client/pages/upload/index.vue
+++ b/client/pages/upload/index.vue
@@ -91,6 +91,7 @@
 <script>
 import Path from 'path'
 import uploadHelpers from '@/mixins/uploadHelpers'
+import globals from '../../../server/utils/globals'
 
 export default {
   mixins: [uploadHelpers],
@@ -359,8 +360,15 @@ export default {
       // Check if path already exists before starting upload
       //  uploading fails if path already exists
       for (const item of items) {
+        const containsBook = item.files.some(file => globals.SupportedEbookTypes.includes(Path.extname(file.name).toLowerCase().slice(1)))
+        const containsAudio = item.files.some(file => globals.SupportedAudioTypes.includes(Path.extname(file.name).toLowerCase().slice(1)))
+
         const exists = await this.$axios
-          .$post(`/api/filesystem/pathexists`, { directory: item.directory, folderPath: this.selectedFolder.fullPath })
+          .$post(`/api/filesystem/pathexists`, { directory: item.directory, folderPath: this.selectedFolder.fullPath, filenames: item.files.map((f) => f.name),
+                      ...(this.selectedLibrary.mediaType === 'podcast'
+                        ? { allowBookFiles: !containsBook, allowAudioFiles: true }
+                        : { allowBookFiles: !containsBook, allowAudioFiles: !containsAudio })
+                    })
           .then((data) => {
             if (data.exists) {
               if (data.libraryItemTitle) {
diff --git a/server/controllers/FileSystemController.js b/server/controllers/FileSystemController.js
index 4b0a94b3..53a3de88 100644
--- a/server/controllers/FileSystemController.js
+++ b/server/controllers/FileSystemController.js
@@ -5,6 +5,7 @@ const fs = require('../libs/fsExtra')
 const { toNumber } = require('../utils/index')
 const fileUtils = require('../utils/fileUtils')
 const Database = require('../Database')
+const { validatePathExists } = require('../utils/fileUtils')
 
 /**
  * @typedef RequestUserObject
@@ -88,7 +89,11 @@ class FileSystemController {
       return res.sendStatus(403)
     }
 
-    const { directory, folderPath } = req.body
+    // filenames - If filenames is provided, the check only returns true if the actual files exist, not just the directory
+    // allowBookFiles - If true, allows containing other book related files (e.g. .pdf, .epub, etc.)
+    // allowAudioFiles - If true, allows containing other audio related files (e.g. .mp3, .m4b, etc.)
+    const { directory, folderPath, filenames, allowBookFiles, allowAudioFiles } = req.body
+
     if (!directory?.length || typeof directory !== 'string' || !folderPath?.length || typeof folderPath !== 'string') {
       Logger.error(`[FileSystemController] Invalid request body: ${JSON.stringify(req.body)}`)
       return res.status(400).json({
@@ -96,6 +101,21 @@ class FileSystemController {
       })
     }
 
+    // Validate filenames: must be undefined or an array of non-empty strings
+    if (filenames !== undefined && (!Array.isArray(filenames) || filenames.some((f) => typeof f !== 'string' || f.trim().length === 0))) {
+      Logger.error(`[FileSystemController] Invalid filenames in request body: ${JSON.stringify(req.body)}`)
+      return res.status(400).json({
+        error: 'Invalid filenames'
+      })
+    }
+
+    if ((allowBookFiles && typeof allowBookFiles !== 'boolean') || (allowAudioFiles && typeof allowAudioFiles !== 'boolean') || (allowBookFiles && allowAudioFiles)) {
+      Logger.error(`[FileSystemController] Invalid allowBookFiles or allowAudioFiles in request body: ${JSON.stringify(req.body)}`)
+      return res.status(400).json({
+        error: 'Invalid allowBookFiles or allowAudioFiles'
+      })
+    }
+
     // Check that library folder exists
     const libraryFolder = await Database.libraryFolderModel.findOne({
       where: {
@@ -113,50 +133,14 @@ class FileSystemController {
       return res.sendStatus(403)
     }
 
-    let filepath = Path.join(libraryFolder.path, directory)
-    filepath = fileUtils.filePathToPOSIX(filepath)
+    const result = await validatePathExists(libraryFolder, directory, filenames, allowBookFiles, allowAudioFiles)
 
-    // Ensure filepath is inside library folder (prevents directory traversal)
-    if (!filepath.startsWith(libraryFolder.path)) {
-      Logger.error(`[FileSystemController] Filepath is not inside library folder: ${filepath}`)
-      return res.sendStatus(400)
-    }
+    if (!result) return res.status(400).end()
 
-    if (await fs.pathExists(filepath)) {
-      return res.json({
-        exists: true
-      })
-    }
+    console.log(`[FileSystemController] Path exists check for "${directory}" in library "${libraryFolder.libraryId}" with filenames "${Array.isArray(filenames) ? filenames.join(', ') : 'N/A'}", allowBookFiles: ${allowBookFiles}, allowAudioFiles: ${allowAudioFiles} - Result: ${result.exists}`)
 
-    // Check if a library item exists in a subdirectory
-    // See: https://github.com/advplyr/audiobookshelf/issues/4146
-    const cleanedDirectory = directory.split('/').filter(Boolean).join('/')
-    if (cleanedDirectory.includes('/')) {
-      // Can only be 2 levels deep
-      const possiblePaths = []
-      const subdir = Path.dirname(directory)
-      possiblePaths.push(fileUtils.filePathToPOSIX(Path.join(folderPath, subdir)))
-      if (subdir.includes('/')) {
-        possiblePaths.push(fileUtils.filePathToPOSIX(Path.join(folderPath, Path.dirname(subdir))))
-      }
-
-      const libraryItem = await Database.libraryItemModel.findOne({
-        where: {
-          path: possiblePaths
-        }
-      })
-
-      if (libraryItem) {
-        return res.json({
-          exists: true,
-          libraryItemTitle: libraryItem.title
-        })
-      }
-    }
-
-    return res.json({
-      exists: false
-    })
+    return res.json(result)
   }
 }
+
 module.exports = new FileSystemController()
diff --git a/server/controllers/MiscController.js b/server/controllers/MiscController.js
index c779bdd6..5d5c718a 100644
--- a/server/controllers/MiscController.js
+++ b/server/controllers/MiscController.js
@@ -6,11 +6,12 @@ const Logger = require('../Logger')
 const SocketAuthority = require('../SocketAuthority')
 const Database = require('../Database')
 const Watcher = require('../Watcher')
+const globals = require('../utils/globals')
 
 const libraryItemFilters = require('../utils/queries/libraryItemFilters')
 const patternValidation = require('../libs/nodeCron/pattern-validation')
 const { isObject, getTitleIgnorePrefix } = require('../utils/index')
-const { sanitizeFilename } = require('../utils/fileUtils')
+const { sanitizeFilename, validatePathExists } = require('../utils/fileUtils')
 
 const TaskManager = require('../managers/TaskManager')
 const adminStats = require('../utils/queries/adminStats')
@@ -43,7 +44,8 @@ class MiscController {
     }
 
     const files = Object.values(req.files)
-    let { title, author, series, folder: folderId, library: libraryId } = req.body
+    // If allowOverwrite is true, it will allow overwriting existing files.
+    let { title, author, series, folder: folderId, library: libraryId, allowOverwrite } = req.body
     // Validate request body
     if (!libraryId || !folderId || typeof libraryId !== 'string' || typeof folderId !== 'string' || !title || typeof title !== 'string') {
       return res.status(400).send('Invalid request body')
@@ -78,6 +80,16 @@ class MiscController {
     const cleanedOutputDirectoryParts = outputDirectoryParts.filter(Boolean).map((part) => sanitizeFilename(part))
     const outputDirectory = Path.join(...[folder.path, ...cleanedOutputDirectoryParts])
 
+    if (allowOverwrite === undefined || allowOverwrite === null || !allowOverwrite) {
+      const containsBook = files.some(file => globals.SupportedEbookTypes.includes(Path.extname(file.name).toLowerCase().slice(1)))
+      const containsAudio = files.some(file => globals.SupportedAudioTypes.includes(Path.extname(file.name).toLowerCase().slice(1)))
+
+      if ((await validatePathExists(folder, outputDirectory, files.map((f) => f.name), !containsBook, library.mediaType === 'podcast' || !containsAudio, true)).exists) {
+        Logger.error(`Upload path already exists: ${outputDirectory}`)
+        return res.status(400).send('Uploaded file already exists')
+      }
+    }
+
     await fs.ensureDir(outputDirectory)
 
     Logger.info(`Uploading ${files.length} files to`, outputDirectory)
diff --git a/server/utils/fileUtils.js b/server/utils/fileUtils.js
index f80c4acd..3d557708 100644
--- a/server/utils/fileUtils.js
+++ b/server/utils/fileUtils.js
@@ -6,6 +6,7 @@ const fs = require('../libs/fsExtra')
 const rra = require('../libs/recursiveReaddirAsync')
 const Logger = require('../Logger')
 const { AudioMimeType } = require('./constants')
+const globals = require('./globals')
 
 /**
  * Make sure folder separator is POSIX for Windows file paths. e.g. "C:\Users\Abs" becomes "C:/Users/Abs"
@@ -577,3 +578,90 @@ async function copyToExisting(srcPath, destPath) {
   })
 }
 module.exports.copyToExisting = copyToExisting
+
+module.exports.validatePathExists = async function validatePathExists(
+  libraryFolder,
+  directory,
+  filenames,
+  allowBookFiles,
+  allowAudioFiles,
+  skipLibraryFolder = false
+) {
+  let filepath = Path.join(skipLibraryFolder ? '' : libraryFolder.path, directory);
+  filepath = filePathToPOSIX(filepath);
+
+  // Ensure filepath is inside library folder (prevents directory traversal)
+  if (!filepath.startsWith(libraryFolder.path)) {
+    Logger.error(
+      `[FileSystemController] Filepath is not inside library folder: ${filepath}`
+    );
+    return null;
+  }
+
+  if (await fs.pathExists(filepath)) {
+    if (filenames && filenames.length > 0) {
+      // If any filename exists, not allowed to upload (exists: true)
+      for (const filename of filenames) {
+        const filePath = Path.join(filepath, filename);
+        if (await fs.pathExists(filePath)) {
+          return {
+            exists: true,
+          };
+        }
+      }
+    }
+    if (allowBookFiles || allowAudioFiles) {
+      let restrictedExtensions = [];
+      if (allowBookFiles && !allowAudioFiles) {
+        restrictedExtensions = globals.SupportedAudioTypes;
+      } else if (allowAudioFiles && !allowBookFiles) {
+        restrictedExtensions = globals.SupportedEbookTypes;
+      } else {
+        restrictedExtensions = []
+      }
+
+      if (restrictedExtensions.length > 0) {
+        const files = await fs.readdir(filepath);
+        const hasRestrictedFiles = files.some((file) => {
+          const ext = Path.extname(file).toLowerCase().replace(/^\./, "");
+          return restrictedExtensions.includes(ext);
+        });
+
+        if (hasRestrictedFiles) {
+          return { exists: true };
+        }
+      }
+    }
+  }
+
+  // Check if a library item exists in a subdirectory
+  // See: https://github.com/advplyr/audiobookshelf/issues/4146
+  // For filenames it does not matter if the file is in a subdirectory or not because the file is not allowed to be created
+  const cleanedDirectory = directory.split('/').filter(Boolean).join('/')
+  if (cleanedDirectory.includes('/')) {
+    // Can only be 2 levels deep
+    const possiblePaths = []
+    const subdir = Path.dirname(directory)
+    possiblePaths.push(fileUtils.filePathToPOSIX(Path.join(folderPath, subdir)))
+    if (subdir.includes('/')) {
+      possiblePaths.push(fileUtils.filePathToPOSIX(Path.join(folderPath, Path.dirname(subdir))))
+    }
+
+    const libraryItem = await Database.libraryItemModel.findOne({
+      where: {
+        path: possiblePaths
+      }
+    })
+
+    if (libraryItem) {
+      return {
+        exists: true,
+        libraryItemTitle: libraryItem.title
+      }
+    }
+  }
+
+  return {
+    exists: false
+  }
+}