diff --git a/client/pages/upload/index.vue b/client/pages/upload/index.vue
index 3612f422..3043382c 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 +360,11 @@ 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, filenames: item.files.map((f) => f.name) })
+          .$post(`/api/filesystem/pathexists`, { directory: item.directory, folderPath: this.selectedFolder.fullPath, filenames: item.files.map((f) => f.name), allowBookFiles: !containsBook, allowAudioFiles: !containsAudio })
           .then((data) => {
             if (data.exists) {
               if (data.libraryItemTitle) {
diff --git a/server/controllers/MiscController.js b/server/controllers/MiscController.js
index 421e5a10..d0057bd1 100644
--- a/server/controllers/MiscController.js
+++ b/server/controllers/MiscController.js
@@ -44,7 +44,8 @@ class MiscController {
     }
 
     const files = Object.values(req.files)
-    let { title, author, series, folder: folderId, library: libraryId } = req.body
+    // If allowAdditionalFiles the upload endpoint allows adding items even if the type of file already exists in the library.
+    let { title, author, series, folder: folderId, library: libraryId, allowAdditionalFiles } = 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')
@@ -79,12 +80,10 @@ class MiscController {
     const cleanedOutputDirectoryParts = outputDirectoryParts.filter(Boolean).map((part) => sanitizeFilename(part))
     const outputDirectory = Path.join(...[folder.path, ...cleanedOutputDirectoryParts])
 
-    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)))
+    const containsBook = allowAdditionalFiles || files.some(file => globals.SupportedEbookTypes.includes(Path.extname(file.name).toLowerCase().slice(1)))
+    const containsAudio = allowAdditionalFiles || files.some(file => globals.SupportedAudioTypes.includes(Path.extname(file.name).toLowerCase().slice(1)))
 
-    console.log(`Uploading files to ${outputDirectory} with containsBook: ${containsBook}, containsAudio: ${containsAudio}`)
-
-    if ((await validatePathExists(folder, outputDirectory, undefined, !containsBook, !containsAudio, true)).exists) {
+    if ((await validatePathExists(folder, outputDirectory, files.map((f) => f.name), !containsBook, !containsAudio, true)).exists) {
       Logger.error(`Upload path already exists: ${outputDirectory}`)
       return res.status(400).send('Uploaded file already exists')
     }
diff --git a/server/utils/fileUtils.js b/server/utils/fileUtils.js
index 774360ea..c6287648 100644
--- a/server/utils/fileUtils.js
+++ b/server/utils/fileUtils.js
@@ -598,8 +598,6 @@ module.exports.validatePathExists = async function validatePathExists(
     return null;
   }
 
-  console.log(`[FileSystemController] Checking if path exists: "${filepath}"`);
-
   if (await fs.pathExists(filepath)) {
     if (filenames && filenames.length > 0) {
       // If any filename exists, not allowed to upload (exists: true)
@@ -611,30 +609,32 @@ module.exports.validatePathExists = async function validatePathExists(
           };
         }
       }
-    } } else if (allowBookFiles || allowAudioFiles) {
-    let restrictedExtensions = [];
-    if (allowBookFiles && !allowAudioFiles) {
-      restrictedExtensions = globals.SupportedAudioTypes; // Block audio files
-    } else if (allowAudioFiles && !allowBookFiles) {
-      restrictedExtensions = globals.SupportedEbookTypes; // Block book files
     }
-
-    console.log(`[FileSystemController] Checking for restricted files in "${filepath}" with extensions: ${restrictedExtensions.join(', ')}`);
-
-    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 };
+    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 };
+        }
+      } else {
+        return {
+          exists: true,
+        };
       }
-    } else {
-      return {
-        exists: true,
-      };
     }
   }