diff --git a/lib/src/services/api/mediafiles/upload.api.dart b/lib/src/services/api/mediafiles/upload.api.dart
index deb7be04..ea4cc518 100644
--- a/lib/src/services/api/mediafiles/upload.api.dart
+++ b/lib/src/services/api/mediafiles/upload.api.dart
@@ -227,46 +227,54 @@ Future<void> finishStartedPreprocessing() async {
           if (!service.originalPath.existsSync() &&
               !service.uploadRequestPath.existsSync()) {
             if (service.storedPath.existsSync()) {
-              // media files was just stored..
-              continue;
-            }
-            if (mediaFile.reuploadRequestedBy != null) {
-              Log.warn(
-                'Reupload requested for ${mediaFile.mediaId} but files are missing. Cancelling reupload but keeping record.',
-              );
-              await twonlyDB.mediaFilesDao.updateMedia(
-                mediaFile.mediaId,
-                const MediaFilesCompanion(
-                  uploadState: Value(UploadState.uploaded),
-                  reuploadRequestedBy: Value(null),
-                ),
-              );
-              continue;
-            }
-
-            final messages = await twonlyDB.messagesDao.getMessagesByMediaId(
-              mediaFile.mediaId,
-            );
-
-            if (messages.isEmpty) {
-              Log.info(
-                'Deleted media files ${mediaFile.mediaId} as originalPath and uploadRequestPath both do not exists and no messages reference it.',
-              );
-              // the file does not exists anymore and no messages reference it.
-              await twonlyDB.mediaFilesDao.deleteMediaFile(mediaFile.mediaId);
+              // media file was stored, we can recover tempPath from storedPath and upload it.
+              try {
+                if (!service.tempPath.existsSync()) {
+                  service.storedPath.copySync(service.tempPath.path);
+                }
+              } catch (e) {
+                Log.error('Error recovering tempPath from storedPath: $e');
+                continue;
+              }
             } else {
-              Log.warn(
-                'Media files ${mediaFile.mediaId} missing but messages still reference it. Keeping record to avoid broken chat history.',
-              );
-              // Just mark as uploaded to stop preprocessing attempts
-              await twonlyDB.mediaFilesDao.updateMedia(
+              if (mediaFile.reuploadRequestedBy != null) {
+                Log.warn(
+                  'Reupload requested for ${mediaFile.mediaId} but files are missing. Cancelling reupload but keeping record.',
+                );
+                await twonlyDB.mediaFilesDao.updateMedia(
+                  mediaFile.mediaId,
+                  const MediaFilesCompanion(
+                    uploadState: Value(UploadState.uploaded),
+                    reuploadRequestedBy: Value(null),
+                  ),
+                );
+                continue;
+              }
+
+              final messages = await twonlyDB.messagesDao.getMessagesByMediaId(
                 mediaFile.mediaId,
-                const MediaFilesCompanion(
-                  uploadState: Value(UploadState.uploaded),
-                ),
               );
+
+              if (messages.isEmpty) {
+                Log.info(
+                  'Deleted media files ${mediaFile.mediaId} as originalPath and uploadRequestPath both do not exists and no messages reference it.',
+                );
+                // the file does not exists anymore and no messages reference it.
+                await twonlyDB.mediaFilesDao.deleteMediaFile(mediaFile.mediaId);
+              } else {
+                Log.warn(
+                  'Media files ${mediaFile.mediaId} missing but messages still reference it. Keeping record to avoid broken chat history.',
+                );
+                // Just mark as uploaded to stop preprocessing attempts
+                await twonlyDB.mediaFilesDao.updateMedia(
+                  mediaFile.mediaId,
+                  const MediaFilesCompanion(
+                    uploadState: Value(UploadState.uploaded),
+                  ),
+                );
+              }
+              continue;
             }
-            continue;
           }
           Log.info(
             'Finishing started preprocessing of ${mediaFile.mediaId} in state ${mediaFile.uploadState}.',
@@ -434,14 +442,38 @@ Future<void> _startBackgroundMediaUploadInternal(
   if (mediaService.mediaFile.uploadState == UploadState.initialized ||
       mediaService.mediaFile.uploadState == UploadState.preprocessing) {
     Log.info(
-      'Hanlding media file ${mediaService.mediaFile.mediaId} in ${mediaService.mediaFile.uploadState}',
+      'Handling media file ${mediaService.mediaFile.mediaId} in ${mediaService.mediaFile.uploadState}',
     );
 
     await mediaService.setUploadState(UploadState.preprocessing);
 
     if (!mediaService.tempPath.existsSync()) {
-      await mediaService.compressMedia();
+      if (mediaService.storedPath.existsSync()) {
+        try {
+          mediaService.storedPath.copySync(mediaService.tempPath.path);
+        } catch (e) {
+          Log.error('Error copying storedPath to tempPath: $e');
+        }
+      } else {
+        await mediaService.compressMedia();
+      }
       if (!mediaService.tempPath.existsSync()) {
+        final messages = await twonlyDB.messagesDao.getMessagesByMediaId(
+          mediaService.mediaFile.mediaId,
+        );
+        if (messages.isEmpty) {
+          Log.warn(
+            'Media files ${mediaService.mediaFile.mediaId} has no original, temp, or stored path. Removing it from DB as files are not existent.',
+          );
+          await twonlyDB.mediaFilesDao.deleteMediaFile(
+            mediaService.mediaFile.mediaId,
+          );
+        } else {
+          Log.warn(
+            'Media files ${mediaService.mediaFile.mediaId} has no original, temp, or stored path, but messages still reference it. Marking as uploaded to stop retries.',
+          );
+          await mediaService.setUploadState(UploadState.uploaded);
+        }
         return;
       }
     }
diff --git a/lib/src/visual/views/chats/chat_messages_components/message_input.dart b/lib/src/visual/views/chats/chat_messages_components/message_input.dart
index 01c879e3..818f7643 100644
--- a/lib/src/visual/views/chats/chat_messages_components/message_input.dart
+++ b/lib/src/visual/views/chats/chat_messages_components/message_input.dart
@@ -103,6 +103,19 @@ class _MessageInputState extends State<MessageInput> {
     widget.textFieldFocus.dispose();
     recorderController.dispose();
     _nextTypingIndicator?.cancel();
+
+    // Persist draft message on close
+    final draftText = _textFieldController.text;
+    unawaited(
+      twonlyDB.groupsDao.updateGroup(
+        widget.group.groupId,
+        GroupsCompanion(
+          draftMessage: Value(draftText.isEmpty ? null : draftText),
+        ),
+      ),
+    );
+    _textFieldController.dispose();
+
     super.dispose();
   }
 
@@ -293,22 +306,15 @@ class _MessageInputState extends State<MessageInput> {
                               TextField(
                                 controller: _textFieldController,
                                 focusNode: widget.textFieldFocus,
-                                textCapitalization: TextCapitalization.sentences,
+                                textCapitalization:
+                                    TextCapitalization.sentences,
                                 keyboardType: TextInputType.multiline,
                                 showCursor:
                                     _recordingState != RecordingState.recording,
                                 maxLines: 4,
                                 minLines: 1,
-                                onChanged: (value) async {
+                                onChanged: (value) {
                                   setState(() {});
-                                  await twonlyDB.groupsDao.updateGroup(
-                                    widget.group.groupId,
-                                    GroupsCompanion(
-                                      draftMessage: Value(
-                                        _textFieldController.text,
-                                      ),
-                                    ),
-                                  );
                                 },
                                 onSubmitted: (_) {
                                   _sendMessage();
diff --git a/lib/src/visual/views/chats/media_viewer.view.dart b/lib/src/visual/views/chats/media_viewer.view.dart
index 02c10e4e..f8b1d150 100644
--- a/lib/src/visual/views/chats/media_viewer.view.dart
+++ b/lib/src/visual/views/chats/media_viewer.view.dart
@@ -106,6 +106,18 @@ class _MediaViewerViewState extends State<MediaViewerView> {
 
     _disposeVideoController();
 
+    // Persist draft message on close
+    final draftText = textMessageController.text;
+    unawaited(
+      twonlyDB.groupsDao.updateGroup(
+        widget.group.groupId,
+        GroupsCompanion(
+          draftMessage: Value(draftText.isEmpty ? null : draftText),
+        ),
+      ),
+    );
+    textMessageController.dispose();
+
     super.dispose();
   }
 
@@ -834,13 +846,8 @@ class _MediaViewerViewState extends State<MediaViewerView> {
                           autofocus: true,
                           controller: textMessageController,
                           textCapitalization: TextCapitalization.sentences,
-                          onChanged: (value) async {
-                            await twonlyDB.groupsDao.updateGroup(
-                              widget.group.groupId,
-                              GroupsCompanion(
-                                draftMessage: Value(textMessageController.text),
-                              ),
-                            );
+                          onChanged: (value) {
+                            setState(() {});
                           },
                           onEditingComplete: () {
                             setState(() {