diff --git a/src/PlanViewer.App/AboutWindow.axaml.cs b/src/PlanViewer.App/AboutWindow.axaml.cs
index 934d8d8..d05e435 100644
--- a/src/PlanViewer.App/AboutWindow.axaml.cs
+++ b/src/PlanViewer.App/AboutWindow.axaml.cs
@@ -132,9 +132,18 @@ private async void CheckUpdate_Click(object? sender, RoutedEventArgs e)
         CheckUpdateButton.IsEnabled = true;
     }
 
+    private bool _updateDownloaded;
+
     private async void UpdateLink_Click(object? sender, PointerPressedEventArgs e)
     {
-        // Velopack download + apply
+        // Step 3: User clicks "Restart now" after download
+        if (_updateDownloaded && _velopackMgr != null && _velopackUpdate != null)
+        {
+            _velopackMgr.ApplyUpdatesAndRestart(_velopackUpdate.TargetFullRelease);
+            return;
+        }
+
+        // Step 2: User clicks to download
         if (_velopackMgr != null && _velopackUpdate != null)
         {
             try
@@ -144,8 +153,10 @@ private async void UpdateLink_Click(object? sender, PointerPressedEventArgs e)
 
                 await _velopackMgr.DownloadUpdatesAsync(_velopackUpdate);
 
-                UpdateStatusText.Text = "Update downloaded — restarting...";
-                _velopackMgr.ApplyUpdatesAndRestart(_velopackUpdate.TargetFullRelease);
+                _updateDownloaded = true;
+                UpdateStatusText.Text = "Update downloaded.";
+                UpdateLink.Text = "Restart now to apply";
+                UpdateLink.IsVisible = true;
             }
             catch (Exception ex)
             {
diff --git a/src/PlanViewer.App/MainWindow.axaml.cs b/src/PlanViewer.App/MainWindow.axaml.cs
index 9254409..81706bf 100644
--- a/src/PlanViewer.App/MainWindow.axaml.cs
+++ b/src/PlanViewer.App/MainWindow.axaml.cs
@@ -48,6 +48,9 @@ public MainWindow()
 
         InitializeComponent();
 
+        // Check for updates on startup (non-blocking)
+        _ = CheckForUpdatesOnStartupAsync();
+
         // Build the Recent Plans submenu from saved state
         RebuildRecentPlansMenu();
 
@@ -1359,4 +1362,52 @@ private void ShowError(string message)
         };
         dialog.ShowDialog(this);
     }
+
+    private async Task CheckForUpdatesOnStartupAsync()
+    {
+        try
+        {
+            await Task.Delay(5000); // Don't slow down startup
+
+            if (System.Runtime.InteropServices.RuntimeInformation.IsOSPlatform(
+                System.Runtime.InteropServices.OSPlatform.Windows))
+            {
+                try
+                {
+                    var mgr = new Velopack.UpdateManager(
+                        new Velopack.Sources.GithubSource(
+                            "https://github.com/erikdarlingdata/PerformanceStudio", null, false));
+
+                    var update = await mgr.CheckForUpdatesAsync();
+                    if (update != null)
+                    {
+                        await Dispatcher.UIThread.InvokeAsync(() =>
+                        {
+                            Title = $"Performance Studio — Update v{update.TargetFullRelease.Version} available (Help > About)";
+                        });
+                        return;
+                    }
+                }
+                catch
+                {
+                    // Velopack not available — fall through
+                }
+            }
+
+            var currentVersion = System.Reflection.Assembly.GetExecutingAssembly().GetName().Version
+                ?? new Version(0, 0, 0);
+            var result = await UpdateChecker.CheckAsync(currentVersion);
+            if (result.UpdateAvailable)
+            {
+                await Dispatcher.UIThread.InvokeAsync(() =>
+                {
+                    Title = $"Performance Studio — Update {result.LatestVersion} available (Help > About)";
+                });
+            }
+        }
+        catch
+        {
+            // Never crash on update check
+        }
+    }
 }