diff --git a/lib/src/database/daos/messages.dao.dart b/lib/src/database/daos/messages.dao.dart
index 53556214..4115de9b 100644
--- a/lib/src/database/daos/messages.dao.dart
+++ b/lib/src/database/daos/messages.dao.dart
@@ -184,14 +184,27 @@ class MessagesDao extends DatabaseAccessor<TwonlyDB> with _$MessagesDaoMixin {
       return;
     }
     if (msg.mediaId != null && contactId != null) {
-      // contactId -> When a image is send to multiple and one message is delete the image should be still available...
-      await (delete(
-        mediaFiles,
-      )..where((t) => t.mediaId.equals(msg.mediaId!))).go();
+      final otherMessagesWithSameMedia = await (select(messages)
+            ..where(
+              (t) =>
+                  t.mediaId.equals(msg.mediaId!) &
+                  t.messageId.equals(messageId).not(),
+            ))
+          .get();
 
-      final mediaService = await MediaFileService.fromMediaId(msg.mediaId!);
-      if (mediaService != null) {
-        mediaService.fullMediaRemoval();
+      if (otherMessagesWithSameMedia.isEmpty) {
+        await (delete(
+          mediaFiles,
+        )..where((t) => t.mediaId.equals(msg.mediaId!))).go();
+
+        final mediaService = await MediaFileService.fromMediaId(msg.mediaId!);
+        if (mediaService != null) {
+          mediaService.fullMediaRemoval();
+        }
+      } else {
+        Log.info(
+          'Media ${msg.mediaId} is still used by ${otherMessagesWithSameMedia.length} other messages. Skipping physical deletion.',
+        );
       }
     }
     await (delete(
diff --git a/lib/src/services/api/mediafiles/upload.api.dart b/lib/src/services/api/mediafiles/upload.api.dart
index 2e7dc975..60a28e37 100644
--- a/lib/src/services/api/mediafiles/upload.api.dart
+++ b/lib/src/services/api/mediafiles/upload.api.dart
@@ -204,11 +204,42 @@ Future<void> finishStartedPreprocessing() async {
           // media files was just stored..
           continue;
         }
-        Log.info(
-          'Deleted media files, as originalPath and uploadRequestPath both do not exists',
+        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,
         );
-        // the file does not exists anymore.
-        await twonlyDB.mediaFilesDao.deleteMediaFile(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);
+        } 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;
       }
       Log.info(
diff --git a/lib/src/services/mediafiles/mediafile.service.dart b/lib/src/services/mediafiles/mediafile.service.dart
index daffe410..7f08c4f4 100644
--- a/lib/src/services/mediafiles/mediafile.service.dart
+++ b/lib/src/services/mediafiles/mediafile.service.dart
@@ -78,7 +78,7 @@ class MediaFileService {
                 final group = await twonlyDB.groupsDao.getGroup(
                   message.groupId,
                 );
-                if (group != null && !group.isDirectChat) {
+                if (group != null) {
                   delete = false;
                 }
               }