diff --git a/crates/matrix-sdk-ui/tests/integration/timeline/media.rs b/crates/matrix-sdk-ui/tests/integration/timeline/media.rs
new file mode 100644
index 00000000000..ef5cb20d163
--- /dev/null
+++ b/crates/matrix-sdk-ui/tests/integration/timeline/media.rs
@@ -0,0 +1,141 @@
+// Copyright 2024 The Matrix.org Foundation C.I.C.
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+use std::{fs::File, io::Write as _, time::Duration};
+
+use assert_matches::assert_matches;
+use assert_matches2::assert_let;
+use eyeball_im::VectorDiff;
+use futures_util::{FutureExt, StreamExt};
+use matrix_sdk::{
+    assert_let_timeout,
+    attachment::AttachmentConfig,
+    test_utils::{events::EventFactory, mocks::MatrixMockServer},
+};
+use matrix_sdk_test::{async_test, JoinedRoomBuilder, ALICE};
+use matrix_sdk_ui::timeline::{EventSendState, RoomExt, TimelineItemContent};
+use ruma::{
+    event_id,
+    events::room::{message::MessageType, MediaSource},
+    room_id,
+};
+use serde_json::json;
+use tempfile::TempDir;
+use tokio::time::sleep;
+use wiremock::ResponseTemplate;
+
+#[async_test]
+async fn test_send_attachment() {
+    let mock = MatrixMockServer::new().await;
+    let client = mock.client_builder().build().await;
+
+    mock.mock_room_state_encryption().plain().mount().await;
+
+    let room_id = room_id!("!a98sd12bjh:example.org");
+    let room = mock.sync_joined_room(&client, room_id).await;
+    let timeline = room.timeline().await.unwrap();
+
+    let (items, mut timeline_stream) =
+        timeline.subscribe_filter_map(|item| item.as_event().cloned()).await;
+    assert!(items.is_empty());
+
+    let f = EventFactory::new();
+    mock.sync_room(
+        &client,
+        JoinedRoomBuilder::new(room_id).add_timeline_event(f.text_msg("hello").sender(&ALICE)),
+    )
+    .await;
+
+    // Sanity check.
+    assert_let_timeout!(Some(VectorDiff::PushBack { value: item }) = timeline_stream.next());
+    assert_let!(TimelineItemContent::Message(msg) = item.content());
+    assert_eq!(msg.body(), "hello");
+
+    // No other updates.
+    assert!(timeline_stream.next().now_or_never().is_none());
+
+    // Store a file in a temporary directory.
+    let tmp_dir = TempDir::new().unwrap();
+
+    let file_path = tmp_dir.path().join("test.bin");
+    {
+        let mut file = File::create(&file_path).unwrap();
+        file.write_all(b"hello world").unwrap();
+    }
+
+    // Set up mocks for the file upload.
+    mock.mock_upload()
+        .respond_with(ResponseTemplate::new(200).set_delay(Duration::from_secs(2)).set_body_json(
+            json!({
+              "content_uri": "mxc://sdk.rs/media"
+            }),
+        ))
+        .mock_once()
+        .mount()
+        .await;
+
+    mock.mock_room_send().ok(event_id!("$media")).mock_once().mount().await;
+
+    // Queue sending of an attachment.
+    let config = AttachmentConfig::new().caption(Some("caption".to_owned()));
+    timeline.send_attachment(&file_path, mime::TEXT_PLAIN, config).use_send_queue().await.unwrap();
+
+    {
+        assert_let_timeout!(Some(VectorDiff::PushBack { value: item }) = timeline_stream.next());
+        assert_matches!(item.send_state(), Some(EventSendState::NotSentYet));
+
+        assert_let!(TimelineItemContent::Message(msg) = item.content());
+
+        // Body is the caption, because there's both a caption and filename.
+        assert_eq!(msg.body(), "caption");
+        assert_let!(MessageType::File(file) = msg.msgtype());
+        assert_eq!(file.filename(), "test.bin");
+        assert_eq!(file.caption(), Some("caption"));
+
+        // The URI refers to the local cache.
+        assert_let!(MediaSource::Plain(uri) = &file.source);
+        assert!(uri.to_string().contains("localhost"));
+    }
+
+    // Eventually, the media is updated with the final MXC IDs…
+    sleep(Duration::from_secs(2)).await;
+
+    {
+        assert_let_timeout!(
+            Some(VectorDiff::Set { index: 1, value: item }) = timeline_stream.next()
+        );
+        assert_let!(TimelineItemContent::Message(msg) = item.content());
+
+        assert_let!(MessageType::File(file) = msg.msgtype());
+        assert_eq!(file.filename(), "test.bin");
+        assert_eq!(file.caption(), Some("caption"));
+
+        // The URI now refers to the final MXC URI.
+        assert_let!(MediaSource::Plain(uri) = &file.source);
+        assert_eq!(uri.to_string(), "mxc://sdk.rs/media");
+    }
+
+    // And eventually the event itself is sent.
+    {
+        assert_let_timeout!(
+            Some(VectorDiff::Set { index: 1, value: item }) = timeline_stream.next()
+        );
+        assert_matches!(item.send_state(), Some(EventSendState::Sent{ event_id }) => {
+            assert_eq!(event_id, event_id!("$media"));
+        });
+    }
+
+    // That's all, folks!
+    assert!(timeline_stream.next().now_or_never().is_none());
+}
diff --git a/crates/matrix-sdk-ui/tests/integration/timeline/mod.rs b/crates/matrix-sdk-ui/tests/integration/timeline/mod.rs
index b6bc4211140..a70f3a499ff 100644
--- a/crates/matrix-sdk-ui/tests/integration/timeline/mod.rs
+++ b/crates/matrix-sdk-ui/tests/integration/timeline/mod.rs
@@ -53,6 +53,7 @@ use crate::mock_sync;
 mod echo;
 mod edit;
 mod focus_event;
+mod media;
 mod pagination;
 mod pinned_event;
 mod profiles;