diff --git a/crates/matrix-sdk-ui/Cargo.toml b/crates/matrix-sdk-ui/Cargo.toml
index 0026107d5..ff89ec8d3 100644
--- a/crates/matrix-sdk-ui/Cargo.toml
+++ b/crates/matrix-sdk-ui/Cargo.toml
@@ -14,7 +14,7 @@ rustls-tls = ["matrix-sdk/rustls-tls"]
 experimental-room-list = ["experimental-sliding-sync", "dep:async-stream", "dep:eyeball-im-util"]
 experimental-sliding-sync = ["matrix-sdk/experimental-sliding-sync"]
 
-testing = ["matrix-sdk/testing"]
+testing = ["matrix-sdk/testing", "dep:eyeball-im-util"]
 
 [dependencies]
 async-once-cell = "0.5.2"
diff --git a/crates/matrix-sdk-ui/src/timeline/inner.rs b/crates/matrix-sdk-ui/src/timeline/inner.rs
index 5494c8fae..082ddf8b6 100644
--- a/crates/matrix-sdk-ui/src/timeline/inner.rs
+++ b/crates/matrix-sdk-ui/src/timeline/inner.rs
@@ -18,6 +18,8 @@ use std::{collections::HashMap, sync::Arc};
 
 use async_trait::async_trait;
 use eyeball_im::{ObservableVector, VectorSubscriber};
+#[cfg(feature = "testing")]
+use eyeball_im_util::{FilterMapVectorSubscriber, VectorExt};
 use imbl::Vector;
 use indexmap::{IndexMap, IndexSet};
 #[cfg(all(test, feature = "e2e-encryption"))]
@@ -126,6 +128,20 @@ impl<P: RoomDataProvider> TimelineInner<P> {
         (items, stream)
     }
 
+    #[cfg(feature = "testing")]
+    pub(super) async fn subscribe_filter_map<U, F>(
+        &self,
+        f: F,
+    ) -> (Vector<U>, FilterMapVectorSubscriber<Arc<TimelineItem>, F>)
+    where
+        U: Clone,
+        F: Fn(Arc<TimelineItem>) -> Option<U>,
+    {
+        trace!("Creating timeline items signal");
+        let state = self.state.lock().await;
+        state.items.subscribe_filter_map(f)
+    }
+
     pub(super) fn set_initial_user_receipt(
         &mut self,
         receipt_type: ReceiptType,
diff --git a/crates/matrix-sdk-ui/src/timeline/mod.rs b/crates/matrix-sdk-ui/src/timeline/mod.rs
index 768c40f9e..d1fb5f0bd 100644
--- a/crates/matrix-sdk-ui/src/timeline/mod.rs
+++ b/crates/matrix-sdk-ui/src/timeline/mod.rs
@@ -18,7 +18,7 @@
 
 use std::{fs, path::Path, pin::Pin, sync::Arc, task::Poll};
 
-use eyeball_im::{VectorDiff, VectorSubscriber};
+use eyeball_im::VectorDiff;
 use futures_core::Stream;
 use futures_util::TryFutureExt;
 use imbl::Vector;
@@ -244,6 +244,16 @@ impl Timeline {
         (items, stream)
     }
 
+    #[cfg(feature = "testing")]
+    pub async fn subscribe_filter_map<U: Clone>(
+        &self,
+        f: impl Fn(Arc<TimelineItem>) -> Option<U>,
+    ) -> (Vector<U>, impl Stream<Item = VectorDiff<U>>) {
+        let (items, stream) = self.inner.subscribe_filter_map(f).await;
+        let stream = TimelineStream::new(stream, self.drop_handle.clone());
+        (items, stream)
+    }
+
     /// Send a message to the room, and add it to the timeline as a local echo.
     ///
     /// For simplicity, this method doesn't currently allow custom message
@@ -552,24 +562,21 @@ impl Drop for TimelineDropHandle {
 }
 
 pin_project! {
-    struct TimelineStream {
+    struct TimelineStream<S> {
         #[pin]
-        inner: VectorSubscriber<Arc<TimelineItem>>,
+        inner: S,
         event_handler_handles: Arc<TimelineDropHandle>,
     }
 }
 
-impl TimelineStream {
-    fn new(
-        inner: VectorSubscriber<Arc<TimelineItem>>,
-        event_handler_handles: Arc<TimelineDropHandle>,
-    ) -> Self {
+impl<S> TimelineStream<S> {
+    fn new(inner: S, event_handler_handles: Arc<TimelineDropHandle>) -> Self {
         Self { inner, event_handler_handles }
     }
 }
 
-impl Stream for TimelineStream {
-    type Item = VectorDiff<Arc<TimelineItem>>;
+impl<S: Stream> Stream for TimelineStream<S> {
+    type Item = S::Item;
 
     fn poll_next(
         self: Pin<&mut Self>,
diff --git a/crates/matrix-sdk-ui/tests/integration/timeline/echo.rs b/crates/matrix-sdk-ui/tests/integration/timeline/echo.rs
index a8b22a041..1f8f4f808 100644
--- a/crates/matrix-sdk-ui/tests/integration/timeline/echo.rs
+++ b/crates/matrix-sdk-ui/tests/integration/timeline/echo.rs
@@ -133,6 +133,60 @@ async fn echo() {
     assert_eq!(item.timestamp(), MilliSecondsSinceUnixEpoch(uint!(152038280)));
 }
 
+#[async_test]
+async fn retry_failed() {
+    let room_id = room_id!("!a98sd12bjh:example.org");
+    let (client, server) = logged_in_client().await;
+    let sync_settings = SyncSettings::new().timeout(Duration::from_millis(3000));
+
+    let mut ev_builder = EventBuilder::new();
+    ev_builder.add_joined_room(JoinedRoomBuilder::new(room_id));
+
+    mock_sync(&server, ev_builder.build_json_sync_response(), None).await;
+    let _response = client.sync_once(sync_settings.clone()).await.unwrap();
+    server.reset().await;
+
+    let room = client.get_room(room_id).unwrap();
+    let timeline = Arc::new(room.timeline().await);
+    let (_, mut timeline_stream) =
+        timeline.subscribe_filter_map(|item| item.as_event().cloned()).await;
+
+    let event_id = event_id!("$wWgymRfo7ri1uQx0NXO40vLJ");
+    let txn_id: &TransactionId = "my-txn-id".into();
+
+    timeline.send(RoomMessageEventContent::text_plain("Hello, World!").into(), Some(txn_id)).await;
+
+    // First, local echo is added
+    assert_next_matches!(timeline_stream, VectorDiff::PushBack { value } => {
+        assert_matches!(value.send_state(), Some(EventSendState::NotSentYet));
+    });
+
+    // Sending fails, the mock server has no matching route yet
+    assert_next_matches!(timeline_stream, VectorDiff::Set { index: 0, value } => {
+        assert_matches!(value.send_state(), Some(EventSendState::SendingFailed { .. }));
+    });
+
+    Mock::given(method("PUT"))
+        .and(path_regex(r"^/_matrix/client/r0/rooms/.*/send/.*"))
+        .and(header("authorization", "Bearer 1234"))
+        .respond_with(ResponseTemplate::new(200).set_body_json(&json!({ "event_id": event_id })))
+        .mount(&server)
+        .await;
+
+    timeline.retry_send(txn_id).await.unwrap();
+
+    // 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_matches!(value.send_state(), Some(EventSendState::NotSentYet));
+    });
+
+    // … before succeeding.
+    assert_next_matches!(timeline_stream, VectorDiff::Set { index: 0, value } => {
+        assert_matches!(value.send_state(), Some(EventSendState::Sent { .. }));
+    });
+}
+
 #[async_test]
 async fn dedup_by_event_id_late() {
     let room_id = room_id!("!a98sd12bjh:example.org");