diff --git a/crates/matrix-sdk-ui/src/timeline/inner/mod.rs b/crates/matrix-sdk-ui/src/timeline/inner/mod.rs
index 56031535d..4323ad159 100644
--- a/crates/matrix-sdk-ui/src/timeline/inner/mod.rs
+++ b/crates/matrix-sdk-ui/src/timeline/inner/mod.rs
@@ -723,7 +723,11 @@ impl<P: RoomDataProvider> TimelineInner<P> {
             // reflected in the timeline, so we set all other pending events to
             // cancelled.
             //
-            // TODO(bnjbvr): spooky action at a distance here^
+            // TODO(bnjbvr): spooky action at a distance here^. The sending task is the one
+            // deciding to clear the sending queue, so we're updating based on that implicit
+            // knowledge here. Instead, the sending queue should notify the timeline that
+            // it's deciding to not send those messages, and then only the
+            // timeline should mark these items as cancelled.
             let items = &mut txn.items;
             let num_items = items.len();
             for idx in 0..num_items {
diff --git a/crates/matrix-sdk-ui/src/timeline/mod.rs b/crates/matrix-sdk-ui/src/timeline/mod.rs
index 109010960..5c6e147ea 100644
--- a/crates/matrix-sdk-ui/src/timeline/mod.rs
+++ b/crates/matrix-sdk-ui/src/timeline/mod.rs
@@ -586,7 +586,7 @@ impl Timeline {
             | TimelineItemContent::ProfileChange(_)
             | TimelineItemContent::OtherState(_)
             | TimelineItemContent::CallInvite => {
-                error_return!("Retrying state events/call invite is not currently supported");
+                error_return!("Retrying state events/call invites is not currently supported");
             }
             TimelineItemContent::FailedToParseMessageLike { .. }
             | TimelineItemContent::FailedToParseState { .. } => {
diff --git a/crates/matrix-sdk-ui/src/timeline/queue.rs b/crates/matrix-sdk-ui/src/timeline/queue.rs
index 6e8d6ebdb..b99836aa2 100644
--- a/crates/matrix-sdk-ui/src/timeline/queue.rs
+++ b/crates/matrix-sdk-ui/src/timeline/queue.rs
@@ -115,7 +115,9 @@ async fn send_or_queue_msg(
         return;
     }
 
-    if room.state() != RoomState::Joined {
+    if room.state() == RoomState::Joined {
+        send_task.start(room, msg);
+    } else {
         info!("Refusing to send message, room is not joined");
         timeline
             .update_event_send_state(
@@ -126,10 +128,7 @@ async fn send_or_queue_msg(
                 },
             )
             .await;
-        return;
     }
-
-    send_task.start(room, msg);
 }
 
 async fn handle_send_result(