diff --git a/osu.Desktop/Updater/VelopackUpdateManager.cs b/osu.Desktop/Updater/VelopackUpdateManager.cs
index e550755fffea..ae58a8793c2d 100644
--- a/osu.Desktop/Updater/VelopackUpdateManager.cs
+++ b/osu.Desktop/Updater/VelopackUpdateManager.cs
@@ -45,14 +45,17 @@ private void load(INotificationOverlay notifications)
 
         private async Task<bool> checkForUpdateAsync(UpdateProgressNotification? notification = null)
         {
-            // should we schedule a retry on completion of this check?
-            bool scheduleRecheck = true;
+            // whether to check again in 30 minutes. generally only if there's an error or no update was found (yet).
+            bool scheduleRecheck = false;
 
             try
             {
                 // Avoid any kind of update checking while gameplay is running.
                 if (localUserInfo?.IsPlaying.Value == true)
+                {
+                    scheduleRecheck = true;
                     return false;
+                }
 
                 // TODO: we should probably be checking if there's a more recent update, rather than shortcutting here.
                 // Velopack does support this scenario (see https://github.com/ppy/osu/pull/28743#discussion_r1743495975).
@@ -67,17 +70,20 @@ private async Task<bool> checkForUpdateAsync(UpdateProgressNotification? notific
                             return true;
                         }
                     });
+
                     return true;
                 }
 
                 pendingUpdate = await updateManager.CheckForUpdatesAsync().ConfigureAwait(false);
 
-                // Handle no updates available.
+                // No update is available. We'll check again later.
                 if (pendingUpdate == null)
+                {
+                    scheduleRecheck = true;
                     return false;
+                }
 
-                scheduleRecheck = false;
-
+                // An update is found, let's notify the user and start downloading it.
                 if (notification == null)
                 {
                     notification = new UpdateProgressNotification
@@ -99,6 +105,7 @@ private async Task<bool> checkForUpdateAsync(UpdateProgressNotification? notific
                 catch (Exception e)
                 {
                     // In the case of an error, a separate notification will be displayed.
+                    scheduleRecheck = true;
                     notification.FailDownload();
                     Logger.Error(e, @"update failed!");
                 }
@@ -113,7 +120,6 @@ private async Task<bool> checkForUpdateAsync(UpdateProgressNotification? notific
             {
                 if (scheduleRecheck)
                 {
-                    // check again in 30 minutes.
                     Scheduler.AddDelayed(() => Task.Run(async () => await checkForUpdateAsync().ConfigureAwait(false)), 60000 * 30);
                 }
             }