diff --git a/Cargo.lock b/Cargo.lock
index 8e563096..daad96f7 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -1442,6 +1442,7 @@ dependencies = [
  "strum",
  "thiserror",
  "tokio",
+ "tokio-stream",
  "tracing",
  "tracing-subscriber",
  "url",
diff --git a/Cargo.toml b/Cargo.toml
index dc143728..b690f65a 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -44,6 +44,7 @@ serde_json = "1"
 strum = { version = "0.26", features = ["derive"] }
 thiserror = "1"
 tokio = { version = "1", features = ["rt", "rt-multi-thread", "sync"] }
+tokio-stream = { version = "0.1", features = ["sync"] }
 tracing = "0.1"
 tracing-subscriber = { version = "0.3", features = ["env-filter"] }
 url = "2"
diff --git a/src/session/model/room/mod.rs b/src/session/model/room/mod.rs
index 21041985..1c4e9c9e 100644
--- a/src/session/model/room/mod.rs
+++ b/src/session/model/room/mod.rs
@@ -12,10 +12,12 @@ use matrix_sdk::{
     deserialized_responses::{AmbiguityChange, MemberEvent, SyncTimelineEvent},
     event_handler::EventHandlerDropGuard,
     room::Room as MatrixRoom,
+    send_queue::RoomSendQueueUpdate,
     sync::{JoinedRoomUpdate, LeftRoomUpdate},
     DisplayName, Result as MatrixResult, RoomInfo, RoomMemberships, RoomState,
 };
 use ruma::{
+    api::client::error::{ErrorKind, RetryAfter},
     events::{
         receipt::{ReceiptEventContent, ReceiptType},
         relation::Annotation,
@@ -30,6 +32,7 @@ use ruma::{
     },
     EventId, MatrixToUri, MatrixUri, OwnedEventId, OwnedRoomId, OwnedUserId, RoomId, UserId,
 };
+use tokio_stream::wrappers::BroadcastStream;
 use tracing::{debug, error, warn};
 
 mod aliases;
@@ -67,10 +70,15 @@ use crate::{
     utils::BoundObjectWeakRef,
 };
 
+/// The default duration in seconds that we wait for to retry failed sending
+/// requests.
+const DEFAULT_RETRY_AFTER: u32 = 30;
+
 mod imp {
     use std::{
         cell::{Cell, OnceCell},
         marker::PhantomData,
+        time::SystemTime,
     };
 
     use glib::subclass::Signal;
@@ -364,6 +372,75 @@ mod imp {
             self.notifications_setting.set(setting);
             self.obj().notify_notifications_setting();
         }
+
+        /// Watch errors in the send queue to try to handle them.
+        pub(super) async fn watch_send_queue(&self) {
+            let send_queue = self.matrix_room().send_queue();
+
+            let room_weak = glib::SendWeakRef::from(self.obj().downgrade());
+            spawn_tokio!(async move {
+                let subscriber = match send_queue.subscribe().await {
+                    Ok((_, subscriber)) => BroadcastStream::new(subscriber),
+                    Err(error) => {
+                        warn!("Failed to listen to room send queue: {error}");
+                        return;
+                    }
+                };
+
+                subscriber
+                    .for_each(move |update| {
+                        let room_weak = room_weak.clone();
+                        async move {
+                            let Ok(RoomSendQueueUpdate::SendError {
+                                error,
+                                is_recoverable: true,
+                                ..
+                            }) = update
+                            else {
+                                return;
+                            };
+
+                            let ctx = glib::MainContext::default();
+                            ctx.spawn(async move {
+                                spawn!(async move {
+                                    let Some(obj) = room_weak.upgrade() else {
+                                        return;
+                                    };
+                                    let Some(session) = obj.session() else {
+                                        return;
+                                    };
+
+                                    if session.is_offline() {
+                                        // The queue will be restarted when the session is back
+                                        // online.
+                                        return;
+                                    }
+
+                                    let duration = match error.client_api_error_kind() {
+                                        Some(ErrorKind::LimitExceeded {
+                                            retry_after: Some(retry_after),
+                                        }) => match retry_after {
+                                            RetryAfter::Delay(duration) => Some(*duration),
+                                            RetryAfter::DateTime(time) => {
+                                                time.duration_since(SystemTime::now()).ok()
+                                            }
+                                        },
+                                        _ => None,
+                                    };
+                                    let retry_after = duration
+                                        .and_then(|d| d.as_secs().try_into().ok())
+                                        .unwrap_or(DEFAULT_RETRY_AFTER);
+
+                                    glib::timeout_add_seconds_local_once(retry_after, move || {
+                                        obj.matrix_room().send_queue().set_enabled(true);
+                                    });
+                                });
+                            });
+                        }
+                    })
+                    .await;
+            });
+        }
     }
 }
 
@@ -497,6 +574,17 @@ impl Room {
                 }
             )
         );
+
+        spawn!(
+            glib::Priority::DEFAULT_IDLE,
+            clone!(
+                #[weak(rename_to = obj)]
+                self,
+                async move {
+                    obj.imp().watch_send_queue().await;
+                }
+            )
+        );
     }
 
     fn init_timeline(&self) {