diff --git a/crates/matrix-sdk/tests/integration/send_queue.rs b/crates/matrix-sdk/tests/integration/send_queue.rs
index 6457b3687d3..4198a123d80 100644
--- a/crates/matrix-sdk/tests/integration/send_queue.rs
+++ b/crates/matrix-sdk/tests/integration/send_queue.rs
@@ -44,7 +44,7 @@ use wiremock::{Request, ResponseTemplate};
 /// Queues an attachment whenever the actual data/mime type etc. don't matter.
 ///
 /// Returns the filename, for sanity check purposes.
-async fn queue_attachment_no_thumbnail(q: &RoomSendQueue) -> &'static str {
+async fn queue_attachment_no_thumbnail(q: &RoomSendQueue) -> (SendHandle, &'static str) {
     let filename = "surprise.jpeg.exe";
     let content_type = mime::IMAGE_JPEG;
     let data = b"hello world".to_vec();
@@ -54,10 +54,11 @@ async fn queue_attachment_no_thumbnail(q: &RoomSendQueue) -> &'static str {
         size: Some(uint!(42)),
         blurhash: None,
     }));
-    q.send_attachment(filename, content_type, data, config)
+    let handle = q
+        .send_attachment(filename, content_type, data, config)
         .await
         .expect("queuing the attachment works");
-    filename
+    (handle, filename)
 }
 
 /// Queues an attachment whenever the actual data/mime type etc. don't matter,
@@ -2006,7 +2007,7 @@ async fn test_media_upload_retry() {
 
     // Send the media.
     assert!(watch.is_empty());
-    let filename = queue_attachment_no_thumbnail(&q).await;
+    let (_handle, filename) = queue_attachment_no_thumbnail(&q).await;
 
     // Observe the local echo.
     let (event_txn, _send_handle, content) = assert_update!(watch => local echo event);
@@ -2075,7 +2076,7 @@ async fn test_unwedging_media_upload() {
 
     // Send the media.
     assert!(watch.is_empty());
-    let filename = queue_attachment_no_thumbnail(&q).await;
+    let (_handle, filename) = queue_attachment_no_thumbnail(&q).await;
 
     // Observe the local echo.
     let (event_txn, send_handle, content) = assert_update!(watch => local echo event);
@@ -2196,7 +2197,7 @@ async fn test_media_event_is_sent_in_order() {
     mock.mock_room_send().ok(event_id!("$text")).mock_once().mount().await;
 
     // 2. Queue the media.
-    let filename = queue_attachment_no_thumbnail(&q).await;
+    let (_handle, filename) = queue_attachment_no_thumbnail(&q).await;
 
     // 3. Queue the message.
     q.send(RoomMessageEventContent::text_plain("hello world").into()).await.unwrap();
@@ -2311,12 +2312,68 @@ async fn test_cancel_upload_with_thumbnail_active() {
     // Have the thumbnail upload take forever and time out, if continued. This will
     // be interrupted when aborting, so this will never have to complete.
     mock.mock_upload()
-        .respond_with(ResponseTemplate::new(200).set_delay(Duration::from_secs(60)).set_body_json(
-            json!({
-              "mxc_id": "mxc://sdk.rs/unreachable"
-            }),
-        ))
-        .expect(0)
+        .respond_with(ResponseTemplate::new(200).set_delay(Duration::from_secs(60)))
+        .expect(1)
+        .mount()
+        .await;
+
+    // Send the media.
+    assert!(watch.is_empty());
+
+    let (upload_handle, filename) = queue_attachment_with_thumbnail(&q).await;
+
+    let (upload_txn, _send_handle, content) = assert_update!(watch => local echo event);
+    assert_let!(MessageType::Image(img_content) = content.msgtype);
+    assert_eq!(img_content.filename(), filename);
+
+    // Let the upload request start.
+    sleep(Duration::from_millis(500)).await;
+
+    // Abort the upload.
+    abort_and_verify(&client, &mut watch, img_content, upload_handle, upload_txn).await;
+
+    // To prove we're not waiting for the upload to finish, send a message and
+    // observe it's immediately sent.
+    q.send(RoomMessageEventContent::text_plain("hi").into()).await.unwrap();
+    let (msg_txn, _handle) = assert_update!(watch => local echo { body = "hi" });
+    assert_update!(watch => sent { txn = msg_txn, });
+
+    // That's all, folks!
+    assert!(watch.is_empty());
+}
+
+#[async_test]
+async fn test_cancel_upload_with_uploaded_thumbnail_and_file_active() {
+    let mock = MatrixMockServer::new().await;
+
+    // Mark the room as joined.
+    let room_id = room_id!("!a:b.c");
+    let client = mock.client_builder().build().await;
+    let room = mock.sync_joined_room(&client, room_id).await;
+
+    let q = room.send_queue();
+
+    let (local_echoes, mut watch) = q.subscribe().await.unwrap();
+    assert!(local_echoes.is_empty());
+
+    // Prepare endpoints.
+    mock.mock_room_state_encryption().plain().mount().await;
+    mock.mock_room_send().ok(event_id!("$msg")).mock_once().named("send event").mount().await;
+
+    // Have the thumbnail upload finish early.
+    mock.mock_upload()
+        .ok(mxc_uri!("mxc://sdk.rs/thumbnail"))
+        .mock_once()
+        .named("thumbnail upload")
+        .mount()
+        .await;
+
+    // Have the file upload take forever and time out, if continued. This will
+    // be interrupted when aborting, so this will never have to complete.
+    mock.mock_upload()
+        .respond_with(ResponseTemplate::new(200).set_delay(Duration::from_secs(60)))
+        .expect(1)
+        .named("file upload")
         .mount()
         .await;
 
@@ -2329,6 +2386,12 @@ async fn test_cancel_upload_with_thumbnail_active() {
     assert_let!(MessageType::Image(img_content) = content.msgtype);
     assert_eq!(img_content.filename(), filename);
 
+    // The thumbnail uploads just fine.
+    assert_update!(watch => uploaded { related_to = upload_txn, mxc = mxc_uri!("mxc://sdk.rs/thumbnail") });
+
+    // Let the file upload request start.
+    sleep(Duration::from_millis(500)).await;
+
     // Abort the upload.
     abort_and_verify(&client, &mut watch, img_content, upload_handle, upload_txn).await;
 
@@ -2341,3 +2404,171 @@ async fn test_cancel_upload_with_thumbnail_active() {
     // That's all, folks!
     assert!(watch.is_empty());
 }
+
+#[async_test]
+async fn test_cancel_upload_only_file_with_file_active() {
+    let mock = MatrixMockServer::new().await;
+
+    // Mark the room as joined.
+    let room_id = room_id!("!a:b.c");
+    let client = mock.client_builder().build().await;
+    let room = mock.sync_joined_room(&client, room_id).await;
+
+    let q = room.send_queue();
+
+    let (local_echoes, mut watch) = q.subscribe().await.unwrap();
+    assert!(local_echoes.is_empty());
+
+    // Prepare endpoints.
+    mock.mock_room_state_encryption().plain().mount().await;
+    mock.mock_room_send().ok(event_id!("$msg")).mock_once().named("send event").mount().await;
+
+    // Have the file upload take forever and time out, if continued. This will
+    // be interrupted when aborting, so this will never have to complete.
+    mock.mock_upload()
+        .respond_with(ResponseTemplate::new(200).set_delay(Duration::from_secs(60)))
+        .expect(1)
+        .named("file upload")
+        .mount()
+        .await;
+
+    // Send the media.
+    assert!(watch.is_empty());
+
+    let (upload_handle, filename) = queue_attachment_no_thumbnail(&q).await;
+
+    let (upload_txn, _send_handle, content) = assert_update!(watch => local echo event);
+    assert_let!(MessageType::Image(img_content) = content.msgtype);
+    assert_eq!(img_content.filename(), filename);
+
+    // Let the upload request start.
+    sleep(Duration::from_millis(500)).await;
+
+    // Abort the upload.
+    let aborted = upload_handle.abort().await.unwrap();
+    assert!(aborted, "upload must have been aborted");
+
+    assert_update!(watch => cancelled { txn = upload_txn });
+
+    // The event cache doesn't contain the medias anymore.
+    client
+        .media()
+        .get_media_content(
+            &MediaRequestParameters { source: img_content.source, format: MediaFormat::File },
+            true,
+        )
+        .await
+        .unwrap_err();
+
+    // To prove we're not waiting for the upload to finish, send a message and
+    // observe it's immediately sent.
+    q.send(RoomMessageEventContent::text_plain("hi").into()).await.unwrap();
+    let (msg_txn, _handle) = assert_update!(watch => local echo { body = "hi" });
+    assert_update!(watch => sent { txn = msg_txn, });
+
+    // That's all, folks!
+    assert!(watch.is_empty());
+}
+
+#[async_test]
+async fn test_cancel_upload_while_sending_event() {
+    let mock = MatrixMockServer::new().await;
+
+    // Mark the room as joined.
+    let room_id = room_id!("!a:b.c");
+    let client = mock.client_builder().build().await;
+    let room = mock.sync_joined_room(&client, room_id).await;
+
+    let q = room.send_queue();
+
+    let (local_echoes, mut watch) = q.subscribe().await.unwrap();
+    assert!(local_echoes.is_empty());
+
+    // Prepare endpoints.
+    mock.mock_room_state_encryption().plain().mount().await;
+
+    // File upload will succeed immediately.
+    mock.mock_upload()
+        .ok(mxc_uri!("mxc://sdk.rs/media"))
+        .mock_once()
+        .named("file upload")
+        .mount()
+        .await;
+
+    // Sending of the media event will take 1 second, so we can abort it while it's
+    // happening.
+    mock.mock_room_send()
+        .respond_with(ResponseTemplate::new(200).set_delay(Duration::from_secs(1)).set_body_json(
+            json!({
+              "event_id": "$media"
+            }),
+        ))
+        .mock_once()
+        .named("send event")
+        .mock_once()
+        .mount()
+        .await;
+
+    // A redaction will happen because the abort happens after the event is getting
+    // sent.
+    mock.mock_room_redact().ok(event_id!("$redaction")).mock_once().mount().await;
+
+    // Send the media.
+    assert!(watch.is_empty());
+
+    let (upload_handle, filename) = queue_attachment_no_thumbnail(&q).await;
+
+    let (upload_txn, _send_handle, content) = assert_update!(watch => local echo event);
+    assert_let!(MessageType::Image(local_content) = content.msgtype);
+    assert_eq!(local_content.filename(), filename);
+
+    assert_update!(watch => uploaded { related_to = upload_txn, mxc = mxc_uri!("mxc://sdk.rs/media") });
+
+    let edit_msg = assert_update!(watch => edit local echo { txn = upload_txn });
+    assert_let!(MessageType::Image(remote_content) = edit_msg.msgtype);
+    assert_let!(MediaSource::Plain(new_uri) = &remote_content.source);
+    assert_eq!(new_uri, mxc_uri!("mxc://sdk.rs/media"));
+
+    // Let the upload request start.
+    sleep(Duration::from_millis(250)).await;
+
+    // Abort the upload.
+    let aborted = upload_handle.abort().await.unwrap();
+    assert!(aborted, "upload must have been aborted");
+
+    // We get a local echo for the cancelled media event…
+    assert_update!(watch => cancelled { txn = upload_txn });
+    // …But the event is still sent, before getting redacted.
+    assert_update!(watch => sent { txn = upload_txn, });
+
+    // The event cache doesn't contain the media with the local URI.
+    client
+        .media()
+        .get_media_content(
+            &MediaRequestParameters { source: local_content.source, format: MediaFormat::File },
+            true,
+        )
+        .await
+        .unwrap_err();
+
+    // But it does contain the media with the remote URI, which hasn't been removed
+    // from the remote server.
+    client
+        .media()
+        .get_media_content(
+            &MediaRequestParameters { source: remote_content.source, format: MediaFormat::File },
+            true,
+        )
+        .await
+        .unwrap();
+
+    // Let things settle (and the redaction endpoint be called).
+    sleep(Duration::from_secs(1)).await;
+
+    // Trying to abort after it's been sent/redacted is a no-op
+    let aborted = upload_handle.abort().await.unwrap();
+    assert!(aborted.not());
+
+    // That's all, folks!
+    assert!(watch.is_empty());
+}