diff --git a/lib/src/event.dart b/lib/src/event.dart
index dd71135d..7656e241 100644
--- a/lib/src/event.dart
+++ b/lib/src/event.dart
@@ -116,6 +116,28 @@ class Event extends MatrixEvent {
     }
     this.stateKey = stateKey;
     this.originServerTs = originServerTs;
+
+    // Mark event as failed to send if status is `sending` and event is older
+    // than the timeout. This should not happen with the deprecated Moor
+    // database!
+    if (status == 0 && room?.client?.database != null) {
+      // Age of this event in milliseconds
+      final age = DateTime.now().millisecondsSinceEpoch -
+          originServerTs.millisecondsSinceEpoch;
+
+      if (age > room.client.sendMessageTimeoutSeconds * 1000) {
+        // Update this event in database and open timelines
+        final json = toJson();
+        json['unsigned'] ??= <String, dynamic>{};
+        json['unsigned'][messageSendingStatusKey] = -1;
+        room.client.handleSync(SyncUpdate()
+          ..rooms = (RoomsUpdate()
+            ..join = (<String, JoinedRoomUpdate>{}..[room.id] =
+                (JoinedRoomUpdate()
+                  ..timeline = (TimelineUpdate()
+                    ..events = [MatrixEvent.fromJson(json)])))));
+      }
+    }
   }
 
   static Map<String, dynamic> getMapFromPayload(dynamic payload) {
diff --git a/test/timeline_test.dart b/test/timeline_test.dart
index ab94d0e4..cd6a8882 100644
--- a/test/timeline_test.dart
+++ b/test/timeline_test.dart
@@ -346,7 +346,7 @@ void main() {
             'sender': '@alice:example.com',
             'status': 0,
             'event_id': 'will-fail',
-            'origin_server_ts': testTimeStamp
+            'origin_server_ts': DateTime.now().millisecondsSinceEpoch,
           },
           sortOrder: room.newSortOrder));
       await Future.delayed(Duration(milliseconds: 50));
@@ -380,7 +380,7 @@ void main() {
             'sender': '@alice:example.com',
             'status': 0,
             'event_id': 'transaction',
-            'origin_server_ts': testTimeStamp
+            'origin_server_ts': DateTime.now().millisecondsSinceEpoch,
           },
           sortOrder: room.newSortOrder));
       await Future.delayed(Duration(milliseconds: 50));
@@ -430,7 +430,7 @@ void main() {
             'content': {'msgtype': 'm.text', 'body': 'Testcase'},
             'sender': '@alice:example.com',
             'event_id': 'transaction',
-            'origin_server_ts': testTimeStamp,
+            'origin_server_ts': DateTime.now().millisecondsSinceEpoch,
             'unsigned': {
               messageSendingStatusKey: 0,
               'transaction_id': 'transaction',
@@ -488,7 +488,7 @@ void main() {
             'sender': '@alice:example.com',
             'status': 0,
             'event_id': 'transaction',
-            'origin_server_ts': testTimeStamp
+            'origin_server_ts': DateTime.now().millisecondsSinceEpoch,
           },
           sortOrder: room.newSortOrder));
       await Future.delayed(Duration(milliseconds: 50));
@@ -537,7 +537,7 @@ void main() {
             'sender': '@alice:example.com',
             'status': 0,
             'event_id': 'transaction',
-            'origin_server_ts': testTimeStamp
+            'origin_server_ts': DateTime.now().millisecondsSinceEpoch,
           },
           sortOrder: room.newSortOrder));
       await Future.delayed(Duration(milliseconds: 50));