diff --git a/crates/matrix-sdk-ui/src/timeline/inner.rs b/crates/matrix-sdk-ui/src/timeline/inner.rs
index 321304d3d..808bd8739 100644
--- a/crates/matrix-sdk-ui/src/timeline/inner.rs
+++ b/crates/matrix-sdk-ui/src/timeline/inner.rs
@@ -697,7 +697,8 @@ impl<P: RoomDataProvider> TimelineInner<P> {
 
         let new_item = item.with_inner_kind(local_item.with_send_state(EventSendState::NotSentYet));
         let content = item.content.clone();
-        state.items.set(idx, new_item);
+        state.items.remove(idx);
+        state.items.push_back(new_item);
 
         Some(content)
     }
diff --git a/crates/matrix-sdk-ui/tests/integration/timeline/echo.rs b/crates/matrix-sdk-ui/tests/integration/timeline/echo.rs
index 4d5ea66a3..32529d36c 100644
--- a/crates/matrix-sdk-ui/tests/integration/timeline/echo.rs
+++ b/crates/matrix-sdk-ui/tests/integration/timeline/echo.rs
@@ -177,7 +177,8 @@ async fn retry_failed() {
 
     // After mocking the endpoint and retrying, it first transitions back out of
     // the error state
-    assert_next_matches!(timeline_stream, VectorDiff::Set { index: 0, value } => {
+    assert_next_matches!(timeline_stream, VectorDiff::Remove { index: 0 });
+    assert_next_matches!(timeline_stream, VectorDiff::PushBack { value } => {
         assert_matches!(value.send_state(), Some(EventSendState::NotSentYet));
     });
 
diff --git a/crates/matrix-sdk-ui/tests/integration/timeline/queue.rs b/crates/matrix-sdk-ui/tests/integration/timeline/queue.rs
index c97648c47..ae1ca03b2 100644
--- a/crates/matrix-sdk-ui/tests/integration/timeline/queue.rs
+++ b/crates/matrix-sdk-ui/tests/integration/timeline/queue.rs
@@ -175,12 +175,15 @@ async fn retry_order() {
     timeline.retry_send("2".into()).await.unwrap();
     timeline.retry_send("1".into()).await.unwrap();
 
-    // Both items are immediately updated to indicate they are being sent
-    assert_next_matches!(timeline_stream, VectorDiff::Set { index: 1, value } => {
+    // Both items are immediately updated and moved to the bottom in the order
+    // of the function calls to indicate they are being sent
+    assert_next_matches!(timeline_stream, VectorDiff::Remove { index: 1 });
+    assert_next_matches!(timeline_stream, VectorDiff::PushBack { value } => {
         assert_matches!(value.send_state().unwrap(), EventSendState::NotSentYet);
         assert_eq!(value.content().as_message().unwrap().body(), "Second.");
     });
-    assert_next_matches!(timeline_stream, VectorDiff::Set { index: 0, value } => {
+    assert_next_matches!(timeline_stream, VectorDiff::Remove { index: 0 });
+    assert_next_matches!(timeline_stream, VectorDiff::PushBack { value } => {
         assert_matches!(value.send_state().unwrap(), EventSendState::NotSentYet);
         assert_eq!(value.content().as_message().unwrap().body(), "First!");
     });
@@ -188,14 +191,15 @@ async fn retry_order() {
     // Wait 200ms for the first msg, 100ms for the second, 300ms for overhead
     sleep(Duration::from_millis(600)).await;
 
-    // The second item should be updated first, since it was retried first
-    assert_next_matches!(timeline_stream, VectorDiff::Set { index: 1, value } => {
+    // The second item (now at index 0) should be updated first, since it was
+    // retried first
+    assert_next_matches!(timeline_stream, VectorDiff::Set { index: 0, value } => {
         assert_eq!(value.content().as_message().unwrap().body(), "Second.");
         assert_matches!(value.send_state().unwrap(), EventSendState::Sent { .. });
         assert_eq!(value.event_id().unwrap(), "$5E2kLK/Sg342bgBU9ceEIEPYpbFaqJpZ");
     });
     // Then the first one
-    assert_next_matches!(timeline_stream, VectorDiff::Set { index: 0, value } => {
+    assert_next_matches!(timeline_stream, VectorDiff::Set { index: 1, value } => {
         assert_eq!(value.content().as_message().unwrap().body(), "First!");
         assert_matches!(value.send_state().unwrap(), EventSendState::Sent { .. });
         assert_eq!(value.event_id().unwrap(), "$PyHxV5mYzjetBUT3qZq7V95GOzxb02EP");