diff --git a/psst-gui/src/controller/alert_cleanup.rs b/psst-gui/src/controller/alert_cleanup.rs
new file mode 100644
index 00000000..3f47faf3
--- /dev/null
+++ b/psst-gui/src/controller/alert_cleanup.rs
@@ -0,0 +1,30 @@
+use crate::data::AppState;
+use druid::{widget::Controller, Env, Event, EventCtx, Widget};
+use std::time::Duration;
+
+pub struct AlertCleanupController;
+
+const CLEANUP_INTERVAL: Duration = Duration::from_secs(1);
+
+impl<W: Widget<AppState>> Controller<AppState, W> for AlertCleanupController {
+    fn event(
+        &mut self,
+        child: &mut W,
+        ctx: &mut EventCtx,
+        event: &Event,
+        data: &mut AppState,
+        env: &Env,
+    ) {
+        match event {
+            Event::WindowConnected => {
+                ctx.request_timer(CLEANUP_INTERVAL);
+            }
+            Event::Timer(_) => {
+                data.cleanup_alerts();
+                ctx.request_timer(CLEANUP_INTERVAL);
+            }
+            _ => {}
+        }
+        child.event(ctx, event, data, env)
+    }
+}
diff --git a/psst-gui/src/controller/mod.rs b/psst-gui/src/controller/mod.rs
index 657e23d9..ea3dc830 100644
--- a/psst-gui/src/controller/mod.rs
+++ b/psst-gui/src/controller/mod.rs
@@ -1,4 +1,5 @@
 mod after_delay;
+mod alert_cleanup;
 mod ex_click;
 mod ex_cursor;
 mod ex_scroll;
@@ -13,6 +14,7 @@ mod session;
 mod sort;
 
 pub use after_delay::AfterDelay;
+pub use alert_cleanup::AlertCleanupController;
 pub use ex_click::ExClick;
 pub use ex_cursor::ExCursor;
 pub use ex_scroll::ExScroll;
diff --git a/psst-gui/src/data/mod.rs b/psst-gui/src/data/mod.rs
index 26b2a13e..2c1c33fe 100644
--- a/psst-gui/src/data/mod.rs
+++ b/psst-gui/src/data/mod.rs
@@ -23,7 +23,7 @@ use std::{
         atomic::{AtomicUsize, Ordering},
         Arc,
     },
-    time::Duration,
+    time::{Duration, Instant},
 };
 
 use druid::{
@@ -60,6 +60,8 @@ pub use crate::data::{
     utils::{Cached, Float64, Image, Page},
 };
 
+pub const ALERT_DURATION: Duration = Duration::from_secs(5);
+
 #[derive(Clone, Data, Lens)]
 pub struct AppState {
     #[data(ignore)]
@@ -276,25 +278,33 @@ impl AppState {
 }
 
 impl AppState {
-    pub fn info_alert(&mut self, message: impl Display) {
-        self.alerts.push_back(Alert {
+    pub fn add_alert(&mut self, message: impl Display, style: AlertStyle) {
+        let alert = Alert {
             message: message.to_string().into(),
-            style: AlertStyle::Info,
+            style,
             id: Alert::fresh_id(),
-        });
+            created_at: Instant::now(),
+        };
+        self.alerts.push_back(alert);
+    }
+
+    pub fn info_alert(&mut self, message: impl Display) {
+        self.add_alert(message, AlertStyle::Info);
     }
 
     pub fn error_alert(&mut self, message: impl Display) {
-        self.alerts.push_back(Alert {
-            message: message.to_string().into(),
-            style: AlertStyle::Error,
-            id: Alert::fresh_id(),
-        });
+        self.add_alert(message, AlertStyle::Error);
     }
 
     pub fn dismiss_alert(&mut self, id: usize) {
         self.alerts.retain(|a| a.id != id);
     }
+
+    pub fn cleanup_alerts(&mut self) {
+        let now = Instant::now();
+        self.alerts
+            .retain(|alert| now.duration_since(alert.created_at) < ALERT_DURATION);
+    }
 }
 
 #[derive(Clone, Data, Lens)]
@@ -512,6 +522,7 @@ pub struct Alert {
     pub id: usize,
     pub message: Arc<str>,
     pub style: AlertStyle,
+    pub created_at: Instant,
 }
 
 impl Alert {
diff --git a/psst-gui/src/ui/mod.rs b/psst-gui/src/ui/mod.rs
index 2058ee19..347607bc 100644
--- a/psst-gui/src/ui/mod.rs
+++ b/psst-gui/src/ui/mod.rs
@@ -10,9 +10,12 @@ use druid_shell::Cursor;
 use crate::data::config::SortCriteria;
 use crate::{
     cmd,
-    controller::{AfterDelay, NavController, SessionController, SortController},
+    controller::{
+        AfterDelay, AlertCleanupController, NavController, SessionController, SortController,
+    },
     data::{
         config::SortOrder, Alert, AlertStyle, AppState, Config, Nav, Playable, Playback, Route,
+        ALERT_DURATION,
     },
     widget::{
         icons, icons::SvgIcon, Border, Empty, MyWidgetExt, Overlay, ThemeScope, ViewDispatcher,
@@ -170,7 +173,6 @@ fn root_widget() -> impl Widget<AppState> {
 fn alert_widget() -> impl Widget<AppState> {
     const BG: Key<Color> = Key::new("app.alert.BG");
     const DISMISS_ALERT: Selector<usize> = Selector::new("app.alert.dismiss");
-    const ALERT_DURATION: Duration = Duration::from_secs(5);
 
     List::new(|| {
         Flex::row()
@@ -205,6 +207,7 @@ fn alert_widget() -> impl Widget<AppState> {
     .on_command(DISMISS_ALERT, |_, &id, state| {
         state.dismiss_alert(id);
     })
+    .controller(AlertCleanupController)
 }
 
 fn route_widget() -> impl Widget<AppState> {
diff --git a/psst-gui/src/ui/playback.rs b/psst-gui/src/ui/playback.rs
index 441850ee..aafae069 100644
--- a/psst-gui/src/ui/playback.rs
+++ b/psst-gui/src/ui/playback.rs
@@ -108,9 +108,12 @@ fn playing_item_widget() -> impl Widget<NowPlaying> {
                         ctx.submit_command(cmd::NAVIGATE.with(now_playing.origin.to_nav()));
                     })
                     .context_menu(|now_playing| match &now_playing.item {
-                        Playable::Track(track) => {
-                            track::track_menu(track, &now_playing.library, &now_playing.origin, usize::MAX)
-                        }
+                        Playable::Track(track) => track::track_menu(
+                            track,
+                            &now_playing.library,
+                            &now_playing.origin,
+                            usize::MAX,
+                        ),
                         Playable::Episode(episode) => {
                             episode::episode_menu(episode, &now_playing.library)
                         }