diff --git a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ContextMenuViewModel.cs b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ContextMenuViewModel.cs
index 0263f20464..07c238ab42 100644
--- a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ContextMenuViewModel.cs
+++ b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ContextMenuViewModel.cs
@@ -53,7 +53,7 @@ public partial class ContextMenuViewModel : ObservableObject,
     {
         if (SelectedItem is not null)
         {
-            if (SelectedItem.MoreCommands.Count() > 1)
+            if (SelectedItem.PrimaryCommand is not null || SelectedItem.HasMoreCommands)
             {
                 ContextMenuStack.Clear();
                 PushContextStack(SelectedItem.AllCommands);
diff --git a/src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/CommandBar.xaml.cs b/src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/CommandBar.xaml.cs
index 5666381d82..133a9364f0 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/CommandBar.xaml.cs
+++ b/src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/CommandBar.xaml.cs
@@ -44,13 +44,14 @@ public sealed partial class CommandBar : UserControl,
 
     public void Receive(OpenContextMenuMessage message)
     {
-        if (!ViewModel.ShouldShowContextMenu)
-        {
-            return;
-        }
-
         if (message.Element is null)
         {
+            // This is invoked from the "More" button on the command bar
+            if (!ViewModel.ShouldShowContextMenu)
+            {
+                return;
+            }
+
             _ = DispatcherQueue.TryEnqueue(
                 () =>
                 {
@@ -65,6 +66,7 @@ public sealed partial class CommandBar : UserControl,
         }
         else
         {
+            // This is invoked from a specific element
             _ = DispatcherQueue.TryEnqueue(
             () =>
             {