diff --git a/lib/src/event.dart b/lib/src/event.dart
index 85170d09..4cc0866b 100644
--- a/lib/src/event.dart
+++ b/lib/src/event.dart
@@ -327,13 +327,20 @@ class Event extends MatrixEvent {
   /// Try to send this event again. Only works with events of status -1.
   Future<String?> sendAgain({String? txid}) async {
     if (!status.isError) return null;
+    // If this is a failed file sending event, try to fetch the file from the
+    // database first.
+    final url = getAttachmentUrl();
+    if (url?.scheme == 'local') {
+      final file = await downloadAndDecryptAttachment();
+      return await room.sendFileEvent(file, extraContent: content);
+    }
+
     // we do not remove the event here. It will automatically be updated
     // in the `sendEvent` method to transition -1 -> 0 -> 1 -> 2
-    final newEventId = await room.sendEvent(
+    return await room.sendEvent(
       content,
       txid: txid ?? unsigned?['transaction_id'] ?? eventId,
     );
-    return newEventId;
   }
 
   /// Whether the client is allowed to redact this event.
diff --git a/lib/src/room.dart b/lib/src/room.dart
index c6a1d1e1..edbf1729 100644
--- a/lib/src/room.dart
+++ b/lib/src/room.dart
@@ -695,7 +695,7 @@ class Room {
   /// Set [shrinkImageMaxDimension] to for example `1600` if you want to shrink
   /// your image before sending. This is ignored if the File is not a
   /// [MatrixImageFile].
-  Future<Uri> sendFileEvent(
+  Future<String?> sendFileEvent(
     MatrixFile file, {
     String? txid,
     Event? inReplyTo,
@@ -755,6 +755,7 @@ class Room {
           name: file.name,
           maxDimension: shrinkImageMaxDimension,
           customImageResizer: client.customImageResizer,
+          compute: client.runInBackground,
         );
       }
     }
@@ -859,14 +860,14 @@ class Room {
       },
       if (extraContent != null) ...extraContent,
     };
-    await sendEvent(
+    final eventId = await sendEvent(
       content,
       txid: txid,
       inReplyTo: inReplyTo,
       editEventId: editEventId,
     );
     sendingFilePlaceholders.remove(txid);
-    return uploadResp;
+    return eventId;
   }
 
   Future<String?> _sendContent(
diff --git a/test/room_test.dart b/test/room_test.dart
index 56894bfb..b60c16e7 100644
--- a/test/room_test.dart
+++ b/test/room_test.dart
@@ -745,7 +745,7 @@ void main() {
     test('sendFileEvent', () async {
       final testFile = MatrixFile(bytes: Uint8List(0), name: 'file.jpeg');
       final dynamic resp = await room.sendFileEvent(testFile, txid: 'testtxid');
-      expect(resp.toString(), 'mxc://example.com/AQwafuaFswefuhsfAFAgsw');
+      expect(resp.toString(), '\$event10');
     });
 
     test('pushRuleState', () async {