diff --git a/client/mixins/uploadHelpers.js b/client/mixins/uploadHelpers.js
index cc4b1997..2d7a554f 100644
--- a/client/mixins/uploadHelpers.js
+++ b/client/mixins/uploadHelpers.js
@@ -28,11 +28,11 @@ export default {
       var validOtherFiles = []
       var ignoredFiles = []
       files.forEach((file) => {
-        var filetype = this.checkFileType(file.name)
-        if (!filetype) ignoredFiles.push(file)
+        // var filetype = this.checkFileType(file.name)
+        if (!file.filetype) ignoredFiles.push(file)
         else {
-          file.filetype = filetype
-          if (filetype === 'audio' || (filetype === 'ebook' && mediaType === 'book')) validItemFiles.push(file)
+          // file.filetype = filetype
+          if (file.filetype === 'audio' || (file.filetype === 'ebook' && mediaType === 'book')) validItemFiles.push(file)
           else validOtherFiles.push(file)
         }
       })
@@ -82,12 +82,18 @@ export default {
           items: itemResults,
           ignoredFiles: ignoredFilesInRoot
         }
-      } else {
+      } else if (filetree.some((f) => f.filetype !== 'audio') || mediaType !== 'book') {
         // Single Book drop
         return {
           items: this.itemFromTreeItems(filetree, mediaType),
           ignoredFiles: []
         }
+      } else {
+        // Only audio files dropped so treat each one as an audiobook
+        return {
+          items: filetree.map((audioFile) => ({ itemFiles: [audioFile], otherFiles: [], ignoredFiles: [] })),
+          ignoredFiles: []
+        }
       }
     },
     getFilesDropped(dataTransferItems) {
@@ -95,11 +101,12 @@ export default {
         path: '/',
         items: []
       }
-      function traverseFileTreePromise(item, currtreemap) {
+      function traverseFileTreePromise(item, currtreemap, checkFileType) {
         return new Promise((resolve) => {
           if (item.isFile) {
             item.file((file) => {
               file.filepath = currtreemap.path + file.name //save full path
+              file.filetype = checkFileType(file.name)
               currtreemap.items.push(file)
               resolve(file)
             })
@@ -119,7 +126,7 @@ export default {
               dirReader.readEntries((entries) => {
                 if (entries.length > 0) {
                   for (let entr of entries) {
-                    entriesPromises.push(traverseFileTreePromise(entr, newtreemap))
+                    entriesPromises.push(traverseFileTreePromise(entr, newtreemap, checkFileType))
                   }
                   readEntries()
                 } else {
@@ -135,7 +142,7 @@ export default {
       return new Promise((resolve, reject) => {
         let entriesPromises = []
         for (let it of dataTransferItems) {
-          var filetree = traverseFileTreePromise(it.webkitGetAsEntry(), treemap)
+          var filetree = traverseFileTreePromise(it.webkitGetAsEntry(), treemap, this.checkFileType)
           entriesPromises.push(filetree)
         }
         Promise.all(entriesPromises).then(() => {
@@ -152,7 +159,9 @@ export default {
         ...book
       }
       var firstBookFile = book.itemFiles[0]
-      if (!firstBookFile.filepath) return audiobook // No path
+      if (!firstBookFile.filepath) {
+        return audiobook // No path
+      }
 
       var firstBookPath = Path.dirname(firstBookFile.filepath)
 
@@ -165,6 +174,9 @@ export default {
         if (dirs.length) {
           audiobook.author = dirs.pop()
         }
+      } else {
+        // Use file basename as title
+        audiobook.title = Path.basename(firstBookFile.name, Path.extname(firstBookFile.name))
       }
       return audiobook
     },
@@ -178,7 +190,12 @@ export default {
       if (!firstAudioFile.filepath) return podcast // No path
       var firstPath = Path.dirname(firstAudioFile.filepath)
       var dirs = firstPath.split('/').filter(d => !!d && d !== '.')
-      podcast.title = dirs.length > 1 ? dirs[1] : dirs[0]
+      if (dirs.length) {
+        podcast.title = dirs.length > 1 ? dirs[1] : dirs[0]
+      } else {
+        podcast.title = Path.basename(firstAudioFile.name, Path.extname(firstAudioFile.name))
+      }
+
       return podcast
     },
     cleanItem(item, mediaType, index) {
@@ -188,6 +205,7 @@ export default {
     async getItemsFromDataTransferItems(dataTransferItems, mediaType) {
       var files = await this.getFilesDropped(dataTransferItems)
       if (!files || !files.length) return { error: 'No files found ' }
+
       var itemData = this.fileTreeToItems(files, mediaType)
       if (!itemData.items.length && !itemData.ignoredFiles.length) {
         return { error: 'Invalid file drop' }
@@ -218,9 +236,12 @@ export default {
         else {
           file.filetype = filetype
           if (file.webkitRelativePath) file.filepath = file.webkitRelativePath
+          else file.filepath = file.name
 
           if (filetype === 'audio' || (filetype === 'ebook' && mediaType === 'book')) {
             var dir = file.filepath ? Path.dirname(file.filepath) : ''
+            if (dir === '.') dir = ''
+
             if (!itemMap[dir]) {
               itemMap[dir] = {
                 path: dir,
@@ -246,8 +267,17 @@ export default {
         }
       })
 
+      var items = []
       var index = 1
-      var items = Object.values(itemMap).map(i => this.cleanItem(i, mediaType, index++))
+      // If book media type and all files are audio files then treat each one as an audiobook
+      if (itemMap[''] && !otherFiles.length && mediaType === 'book' && !itemMap[''].itemFiles.some(f => f.filetype !== 'audio')) {
+        items = itemMap[''].itemFiles.map((audioFile) => {
+          return this.cleanItem({ itemFiles: [audioFile], otherFiles: [], ignoredFiles: [] }, mediaType, index++)
+        })
+      } else {
+        items = Object.values(itemMap).map(i => this.cleanItem(i, mediaType, index++))
+      }
+
       return {
         items,
         ignoredFiles: ignoredFiles
diff --git a/client/pages/upload/index.vue b/client/pages/upload/index.vue
index e4dd8311..3abce01d 100644
--- a/client/pages/upload/index.vue
+++ b/client/pages/upload/index.vue
@@ -29,7 +29,9 @@
           </div>
         </div>
         <div class="pt-8 text-center">
-          <p class="text-xs text-white text-opacity-50 font-mono"><strong>Supported File Types: </strong>{{ inputAccept.join(', ') }}</p>
+          <p class="text-xs text-white text-opacity-50 font-mono mb-4"><strong>Supported File Types: </strong>{{ inputAccept.join(', ') }}</p>
+
+          <p class="text-sm text-white text-opacity-70">Folders with media files will be treated as separate library items. <span v-if="selectedLibraryMediaType === 'book'">If uploading only audio files then each audio file will be treated as a separate audiobook.</span></p>
         </div>
       </div>
       <!-- Item list header -->