diff --git a/crates/matrix-sdk/src/send_queue.rs b/crates/matrix-sdk/src/send_queue.rs
index fe88a3f063c..22e41e9b1a1 100644
--- a/crates/matrix-sdk/src/send_queue.rs
+++ b/crates/matrix-sdk/src/send_queue.rs
@@ -338,14 +338,19 @@ impl RoomSendQueue {
                 Err(err) => {
                     warn!(txn_id = %queued_event.transaction_id, "error when sending event: {err}");
 
-                    // Disable the queue after an error.
-                    // See comment in [`SendQueue::disable()`].
-                    globally_enabled.set(false);
-
                     // In this case, we intentionally keep the event in the queue, but mark it as
                     // not being sent anymore.
                     queue.mark_as_not_being_sent(&queued_event.transaction_id).await;
 
+                    // Let observers know about a failure *after* we've marked the item as not
+                    // being sent anymore. Otherwise, there's a possible race where a caller might
+                    // try to remove an item, while it's still marked as being sent, resulting in a
+                    // cancellation failure.
+
+                    // Disable the queue after an error.
+                    // See comment in [`SendQueue::disable()`].
+                    globally_enabled.set(false);
+
                     let _ = updates.send(RoomSendQueueUpdate::SendError {
                         transaction_id: queued_event.transaction_id,
                         error: Arc::new(err),
diff --git a/crates/matrix-sdk/tests/integration/send_queue.rs b/crates/matrix-sdk/tests/integration/send_queue.rs
index e8dc5c25062..e9e974d85ab 100644
--- a/crates/matrix-sdk/tests/integration/send_queue.rs
+++ b/crates/matrix-sdk/tests/integration/send_queue.rs
@@ -633,3 +633,69 @@ async fn test_cancellation() {
 
     assert!(watch.is_empty());
 }
+
+#[async_test]
+async fn test_abort_reenable() {
+    let (client, server) = logged_in_client_with_server().await;
+
+    // Mark the room as joined.
+    let room_id = room_id!("!a:b.c");
+
+    let room = mock_sync_with_new_room(
+        |builder| {
+            builder.add_joined_room(JoinedRoomBuilder::new(room_id));
+        },
+        &client,
+        &server,
+        room_id,
+    )
+    .await;
+
+    let mut global_status = client.sending_queue().subscribe_status();
+
+    assert!(global_status.next_now());
+
+    // When I start with an enabled sending queue,
+    client.sending_queue().enable();
+
+    assert!(client.sending_queue().is_enabled());
+
+    let q = room.sending_queue();
+
+    let (local_echoes, mut watch) = q.subscribe().await;
+
+    assert!(local_echoes.is_empty());
+    assert!(watch.is_empty());
+
+    // One message is queued.
+    let abort_send_handle =
+        q.send(RoomMessageEventContent::text_plain("hey there").into()).await.unwrap();
+
+    // It is first seen as a local echo,
+    assert_let!(
+        Ok(Ok(RoomSendQueueUpdate::NewLocalEvent(LocalEcho {
+            content: AnyMessageLikeEventContent::RoomMessage(msg),
+            ..
+        }))) = timeout(Duration::from_secs(1), watch.recv()).await
+    );
+    assert_eq!(msg.body(), format!("hey there"));
+
+    // Waiting for the global status to report the queue is getting disabled.
+    assert!(!global_status.next().await.unwrap());
+
+    // Aborting the sending should work.
+    assert!(abort_send_handle.abort().await);
+
+    // The room updates will report the error, then the cancelled event, eventually.
+    assert_let!(
+        Ok(Ok(RoomSendQueueUpdate::SendError { .. })) =
+            timeout(Duration::from_secs(1), watch.recv()).await
+    );
+
+    assert_let!(
+        Ok(Ok(RoomSendQueueUpdate::CancelledLocalEvent { .. })) =
+            timeout(Duration::from_secs(1), watch.recv()).await
+    );
+
+    assert!(watch.is_empty());
+}