diff --git a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ShellViewModel.cs b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ShellViewModel.cs
index 40afae6f9c..41db974f5b 100644
--- a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ShellViewModel.cs
+++ b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ShellViewModel.cs
@@ -265,6 +265,9 @@ public partial class ShellViewModel : ObservableObject,
                     throw new NotSupportedException();
                 }
 
+                // Clear command bar, ViewModel initialization can already set new commands if it wants to
+                OnUIThread(() => WeakReferenceMessenger.Default.Send<UpdateCommandBarMessage>(new(null)));
+
                 // Kick off async loading of our ViewModel
                 LoadPageViewModelAsync(pageViewModel, navigationToken)
                     .ContinueWith(
@@ -275,9 +278,6 @@ public partial class ShellViewModel : ObservableObject,
                             {
                                 newCts.Dispose();
                             }
-
-                            // When we're done loading the page, then update the command bar to match
-                            WeakReferenceMessenger.Default.Send<UpdateCommandBarMessage>(new(null));
                         },
                         navigationToken,
                         TaskContinuationOptions.None,
diff --git a/src/modules/cmdpal/Microsoft.CmdPal.UI/ExtViews/ContentPage.xaml.cs b/src/modules/cmdpal/Microsoft.CmdPal.UI/ExtViews/ContentPage.xaml.cs
index e9ab57cfa5..c022d82b34 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.UI/ExtViews/ContentPage.xaml.cs
+++ b/src/modules/cmdpal/Microsoft.CmdPal.UI/ExtViews/ContentPage.xaml.cs
@@ -78,6 +78,12 @@ public sealed partial class ContentPage : Page,
         WeakReferenceMessenger.Default.Unregister<ActivateSecondaryCommandMessage>(this);
 
         // Clean-up event listeners
+        if (e.NavigationMode != NavigationMode.New)
+        {
+            ViewModel?.SafeCleanup();
+            CleanupHelper.Cleanup(this);
+        }
+
         ViewModel = null;
     }