diff --git a/osu.Game/Localisation/GeneralSettingsStrings.cs b/osu.Game/Localisation/GeneralSettingsStrings.cs
index 42623f4632fc..83a3af574c80 100644
--- a/osu.Game/Localisation/GeneralSettingsStrings.cs
+++ b/osu.Game/Localisation/GeneralSettingsStrings.cs
@@ -44,6 +44,11 @@ public static class GeneralSettingsStrings
         /// </summary>
         public static LocalisableString CheckUpdate => new TranslatableString(getKey(@"check_update"), @"Check for updates");
 
+        /// <summary>
+        /// "Checking for updates"
+        /// </summary>
+        public static LocalisableString CheckingForUpdates => new TranslatableString(getKey(@"checking_for_updates"), @"Checking for updates");
+
         /// <summary>
         /// "Open osu! folder"
         /// </summary>
diff --git a/osu.Game/Overlays/Settings/Sections/General/UpdateSettings.cs b/osu.Game/Overlays/Settings/Sections/General/UpdateSettings.cs
index 82cc952e5379..261103173ea3 100644
--- a/osu.Game/Overlays/Settings/Sections/General/UpdateSettings.cs
+++ b/osu.Game/Overlays/Settings/Sections/General/UpdateSettings.cs
@@ -4,7 +4,6 @@
 using System.Threading.Tasks;
 using osu.Framework;
 using osu.Framework.Allocation;
-using osu.Framework.Extensions;
 using osu.Framework.Graphics.Sprites;
 using osu.Framework.Localisation;
 using osu.Framework.Logging;
@@ -13,6 +12,7 @@
 using osu.Framework.Statistics;
 using osu.Game.Configuration;
 using osu.Game.Localisation;
+using osu.Game.Online.Multiplayer;
 using osu.Game.Overlays.Notifications;
 using osu.Game.Overlays.Settings.Sections.Maintenance;
 using osu.Game.Updater;
@@ -36,8 +36,11 @@ public partial class UpdateSettings : SettingsSubsection
         [Resolved]
         private Storage storage { get; set; } = null!;
 
+        [Resolved]
+        private OsuGame? game { get; set; }
+
         [BackgroundDependencyLoader]
-        private void load(OsuConfigManager config, OsuGame? game)
+        private void load(OsuConfigManager config)
         {
             Add(new SettingsEnumDropdown<ReleaseStream>
             {
@@ -50,23 +53,7 @@ private void load(OsuConfigManager config, OsuGame? game)
                 Add(checkForUpdatesButton = new SettingsButton
                 {
                     Text = GeneralSettingsStrings.CheckUpdate,
-                    Action = () =>
-                    {
-                        checkForUpdatesButton.Enabled.Value = false;
-                        Task.Run(updateManager.CheckForUpdateAsync).ContinueWith(task => Schedule(() =>
-                        {
-                            if (!task.GetResultSafely())
-                            {
-                                notifications?.Post(new SimpleNotification
-                                {
-                                    Text = GeneralSettingsStrings.RunningLatestRelease(game!.Version),
-                                    Icon = FontAwesome.Solid.CheckCircle,
-                                });
-                            }
-
-                            checkForUpdatesButton.Enabled.Value = true;
-                        }));
-                    }
+                    Action = () => checkForUpdates().FireAndForget()
                 });
             }
 
@@ -94,6 +81,44 @@ private void load(OsuConfigManager config, OsuGame? game)
             }
         }
 
+        private async Task checkForUpdates()
+        {
+            if (updateManager == null || game == null)
+                return;
+
+            checkForUpdatesButton.Enabled.Value = false;
+
+            var checkingNotification = new ProgressNotification
+            {
+                Text = GeneralSettingsStrings.CheckingForUpdates,
+            };
+            notifications?.Post(checkingNotification);
+
+            try
+            {
+                bool foundUpdate = await updateManager.CheckForUpdateAsync().ConfigureAwait(true);
+
+                if (!foundUpdate)
+                {
+                    notifications?.Post(new SimpleNotification
+                    {
+                        Text = GeneralSettingsStrings.RunningLatestRelease(game.Version),
+                        Icon = FontAwesome.Solid.CheckCircle,
+                    });
+                }
+            }
+            catch
+            {
+            }
+            finally
+            {
+                // This sequence allows the notification to be immediately dismissed.
+                checkingNotification.State = ProgressNotificationState.Cancelled;
+                checkingNotification.Close(false);
+                checkForUpdatesButton.Enabled.Value = true;
+            }
+        }
+
         private void exportLogs()
         {
             ProgressNotification notification = new ProgressNotification