diff --git a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/CommandContextItemViewModel.cs b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/CommandContextItemViewModel.cs
index bc07fca640..68da30a006 100644
--- a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/CommandContextItemViewModel.cs
+++ b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/CommandContextItemViewModel.cs
@@ -5,12 +5,13 @@
 using System.Diagnostics.CodeAnalysis;
 using Microsoft.CmdPal.Core.ViewModels.Models;
 using Microsoft.CommandPalette.Extensions;
-using Microsoft.CommandPalette.Extensions.Toolkit;
 
 namespace Microsoft.CmdPal.Core.ViewModels;
 
 [DynamicallyAccessedMembers(DynamicallyAccessedMemberTypes.All)]
-public partial class CommandContextItemViewModel(ICommandContextItem contextItem, WeakReference<IPageContext> context) : CommandItemViewModel(new(contextItem), context), IContextItemViewModel
+public partial class CommandContextItemViewModel(ICommandContextItem contextItem, WeakReference<IPageContext> context) :
+    CommandItemViewModel(new(contextItem), context),
+    ICommandContextItemViewModel
 {
     private readonly KeyChord nullKeyChord = new(0, 0, 0);
 
@@ -45,3 +46,16 @@ public partial class CommandContextItemViewModel(ICommandContextItem contextItem
             contextItem.RequestedShortcut.ScanCode);
     }
 }
+
+public interface ICommandContextItemViewModel : IContextItemViewModel
+{
+    public string Title { get; }
+
+    public IconInfoViewModel Icon { get; }
+
+    public bool IsCritical { get; }
+
+    public KeyChord? RequestedShortcut { get; }
+
+    public bool HasRequestedShortcut { get; }
+}
diff --git a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ListItemViewModel.cs b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ListItemViewModel.cs
index 09040f5c12..10a447b897 100644
--- a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ListItemViewModel.cs
+++ b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ListItemViewModel.cs
@@ -10,7 +10,7 @@ using Microsoft.CommandPalette.Extensions.Toolkit;
 
 namespace Microsoft.CmdPal.Core.ViewModels;
 
-public partial class ListItemViewModel : CommandItemViewModel, IContextItemViewModel
+public partial class ListItemViewModel : CommandItemViewModel, ICommandContextItemViewModel
 {
     public new ExtensionObject<IListItem> Model { get; }
 
@@ -61,6 +61,12 @@ public partial class ListItemViewModel : CommandItemViewModel, IContextItemViewM
         }
     }
 
+    bool ICommandContextItemViewModel.IsCritical => false;
+
+    KeyChord? ICommandContextItemViewModel.RequestedShortcut => null;
+
+    bool ICommandContextItemViewModel.HasRequestedShortcut => false;
+
     public ListItemViewModel(IListItem model, WeakReference<IPageContext> context)
         : base(new(model), context)
     {
diff --git a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/Messages/PerformCommandMessage.cs b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/Messages/PerformCommandMessage.cs
index 418d7d5196..c9dd4d7bb4 100644
--- a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/Messages/PerformCommandMessage.cs
+++ b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/Messages/PerformCommandMessage.cs
@@ -4,6 +4,7 @@
 
 using Microsoft.CmdPal.Core.ViewModels.Models;
 using Microsoft.CommandPalette.Extensions;
+using Windows.Foundation;
 
 namespace Microsoft.CmdPal.Core.ViewModels.Messages;
 
@@ -20,12 +21,28 @@ public record PerformCommandMessage
 
     public bool TransientPage { get; set; }
 
+    public bool OpenAsFlyout { get; private set; }
+
+    public Point? FlyoutPosition { get; private set; }
+
     public PerformCommandMessage(ExtensionObject<ICommand> command)
     {
         Command = command;
         Context = null;
     }
 
+    public static PerformCommandMessage CreateFlyoutMessage(ExtensionObject<ICommand> command, Point flyoutPosition)
+    {
+        var message = new PerformCommandMessage(command)
+        {
+            WithAnimation = false,
+            TransientPage = true,
+            OpenAsFlyout = true,
+            FlyoutPosition = flyoutPosition,
+        };
+        return message;
+    }
+
     public PerformCommandMessage(ExtensionObject<ICommand> command, ExtensionObject<IListItem> context)
     {
         Command = command;
diff --git a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/Messages/ShowCommandInContextMenuMessage.cs b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/Messages/ShowCommandInContextMenuMessage.cs
new file mode 100644
index 0000000000..8ddca87374
--- /dev/null
+++ b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/Messages/ShowCommandInContextMenuMessage.cs
@@ -0,0 +1,11 @@
+// Copyright (c) Microsoft Corporation
+// The Microsoft Corporation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+using Microsoft.CmdPal.Core.ViewModels.Models;
+using Microsoft.CommandPalette.Extensions;
+using Windows.Foundation;
+
+namespace Microsoft.CmdPal.Core.ViewModels.Messages;
+
+public record ShowCommandInContextMenuMessage(IContextMenuContext Context, Point Position);
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 0b8fb52d44..fed47a0591 100644
--- a/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ShellViewModel.cs
+++ b/src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ShellViewModel.cs
@@ -10,6 +10,7 @@ using Microsoft.CmdPal.Core.Common;
 using Microsoft.CmdPal.Core.ViewModels.Messages;
 using Microsoft.CmdPal.Core.ViewModels.Models;
 using Microsoft.CommandPalette.Extensions;
+using Windows.Foundation;
 
 namespace Microsoft.CmdPal.Core.ViewModels;
 
@@ -136,6 +137,28 @@ public partial class ShellViewModel : ObservableObject,
         return true;
     }
 
+    private async Task ShowPageAsFlyoutAsync(PageViewModel viewModel, Point flyoutPosition, CancellationToken cancellationToken = default)
+    {
+        if (viewModel is not IContextMenuContext ctx)
+        {
+            return;
+        }
+
+        // Instead of doing normal page navigation, we want to open this
+        // page as a flyout anchored to the given position.
+        var initialized = await InitializePageViewModelAsync(viewModel, cancellationToken);
+        if (initialized)
+        {
+            await SetCurrentPageAsync(viewModel, cancellationToken);
+
+            // send message
+            WeakReferenceMessenger.Default.Send(new ShowCommandInContextMenuMessage(ctx, flyoutPosition));
+
+            //// now cleanup navigation
+            // await CleanupNavigationTokenAsync(cancellationToken);
+        }
+    }
+
     private async Task LoadPageViewModelAsync(PageViewModel viewModel, CancellationToken cancellationToken = default)
     {
         var initialized = await InitializePageViewModelAsync(viewModel, cancellationToken);
@@ -215,6 +238,15 @@ public partial class ShellViewModel : ObservableObject,
             _scheduler);
     }
 
+    private async Task CleanupNavigationTokenAsync(CancellationTokenSource cts)
+    {
+        // clean up the navigation token if it's still ours
+        if (Interlocked.CompareExchange(ref _navigationCts, null, cts) == cts)
+        {
+            cts.Dispose();
+        }
+    }
+
     public void Receive(PerformCommandMessage message)
     {
         PerformCommand(message);
@@ -259,62 +291,7 @@ public partial class ShellViewModel : ObservableObject,
             if (command is IPage page)
             {
                 CoreLogger.LogDebug($"Navigating to page");
-
-                var isMainPage = command == _rootPage;
-
-                // Telemetry: Track extension page navigation for session metrics
-                if (host is not null)
-                {
-                    var extensionId = host.GetExtensionDisplayName() ?? "builtin";
-                    var commandId = command?.Id ?? "unknown";
-                    var commandName = command?.Name ?? "unknown";
-                    WeakReferenceMessenger.Default.Send<TelemetryExtensionInvokedMessage>(
-                        new(extensionId, commandId, commandName, true, 0));
-                }
-
-                // Construct our ViewModel of the appropriate type and pass it the UI Thread context.
-                var pageViewModel = _pageViewModelFactory.TryCreatePageViewModel(page, !isMainPage, host!);
-                if (pageViewModel is null)
-                {
-                    CoreLogger.LogError($"Failed to create ViewModel for page {page.GetType().Name}");
-                    throw new NotSupportedException();
-                }
-
-                // -------------------------------------------------------------
-                // Slice it here.
-                // Stuff above this, we need to always do, for both commands in the palette and flyout items
-                //
-                // Below here, this is all specific to navigating the current page of the palette
-                _isNested = !isMainPage;
-                _currentlyTransient = message.TransientPage;
-
-                pageViewModel.IsRootPage = isMainPage;
-                pageViewModel.HasBackButton = IsNested;
-
-                // 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(
-                        (Task t) =>
-                        {
-                            // clean up the navigation token if it's still ours
-                            if (Interlocked.CompareExchange(ref _navigationCts, null, newCts) == newCts)
-                            {
-                                newCts.Dispose();
-                            }
-                        },
-                        navigationToken,
-                        TaskContinuationOptions.None,
-                        _scheduler);
-
-                // While we're loading in the background, immediately move to the next page.
-                NavigateToPageMessage msg = new(pageViewModel, message.WithAnimation, navigationToken, message.TransientPage);
-                WeakReferenceMessenger.Default.Send(msg);
-
-                // Note: Originally we set our page back in the ViewModel here, but that now happens in response to the Frame navigating triggered from the above
-                // See RootFrame_Navigated event handler.
+                StartOpenPage(message, page, host, newCts, navigationToken);
             }
             else if (command is IInvokableCommand invokable)
             {
@@ -466,6 +443,71 @@ public partial class ShellViewModel : ObservableObject,
         }
     }
 
+    private void StartOpenPage(PerformCommandMessage message, IPage page, AppExtensionHost? host, CancellationTokenSource cts, CancellationToken navigationToken)
+    {
+        var isMainPage = page == _rootPage;
+
+        // Telemetry: Track extension page navigation for session metrics
+        // TODO! this block is unsafe
+        if (host is not null)
+        {
+            var extensionId = host.GetExtensionDisplayName() ?? "builtin";
+            var commandId = page.Id ?? "unknown";
+            var commandName = page.Name ?? "unknown";
+            WeakReferenceMessenger.Default.Send<TelemetryExtensionInvokedMessage>(
+                new(extensionId, commandId, commandName, true, 0));
+        }
+
+        // Construct our ViewModel of the appropriate type and pass it the UI Thread context.
+        var pageViewModel = _pageViewModelFactory.TryCreatePageViewModel(page, !isMainPage, host!);
+        if (pageViewModel is null)
+        {
+            CoreLogger.LogError($"Failed to create ViewModel for page {page.GetType().Name}");
+            throw new NotSupportedException();
+        }
+
+        if (pageViewModel is ListViewModel listViewModel
+            && message.OpenAsFlyout
+            && message.FlyoutPosition is Point flyoutPosition)
+        {
+            ShowPageAsFlyoutAsync(listViewModel, flyoutPosition, navigationToken)
+                .ContinueWith(
+                    (Task t) => CleanupNavigationTokenAsync(cts),
+                    navigationToken,
+                    TaskContinuationOptions.None,
+                    _scheduler);
+        }
+
+        // -------------------------------------------------------------
+        // Slice it here.
+        // Stuff above this, we need to always do, for both commands in the palette and flyout items
+        //
+        // Below here, this is all specific to navigating the current page of the palette
+        _isNested = !isMainPage;
+        _currentlyTransient = message.TransientPage;
+
+        pageViewModel.IsRootPage = isMainPage;
+        pageViewModel.HasBackButton = IsNested;
+
+        // 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(
+                (Task t) => CleanupNavigationTokenAsync(cts),
+                navigationToken,
+                TaskContinuationOptions.None,
+                _scheduler);
+
+        // While we're loading in the background, immediately move to the next page.
+        NavigateToPageMessage msg = new(pageViewModel, message.WithAnimation, navigationToken, message.TransientPage);
+        WeakReferenceMessenger.Default.Send(msg);
+
+        // Note: Originally we set our page back in the ViewModel here, but that now happens in response to the Frame navigating triggered from the above
+        // See RootFrame_Navigated event handler.
+    }
+
     public void GoHome(bool withAnimation = true, bool focusSearch = true)
     {
         _rootPageService.GoHome();
diff --git a/src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/ContextMenu.xaml b/src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/ContextMenu.xaml
index 36167717ea..88563f09d9 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/ContextMenu.xaml
+++ b/src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/ContextMenu.xaml
@@ -29,7 +29,7 @@
                 Separator="{StaticResource SeparatorContextMenuViewModelTemplate}" />
 
             <!--  Template for context items in the context item menu  -->
-            <DataTemplate x:Key="DefaultContextMenuViewModelTemplate" x:DataType="coreViewModels:CommandContextItemViewModel">
+            <DataTemplate x:Key="DefaultContextMenuViewModelTemplate" x:DataType="coreViewModels:ICommandContextItemViewModel">
                 <Grid Padding="{StaticResource DefaultContextMenuItemPadding}" AutomationProperties.Name="{x:Bind Title, Mode=OneWay}">
                     <Grid.ColumnDefinitions>
                         <ColumnDefinition Width="32" />
diff --git a/src/modules/cmdpal/Microsoft.CmdPal.UI/Dock/DockControl.xaml.cs b/src/modules/cmdpal/Microsoft.CmdPal.UI/Dock/DockControl.xaml.cs
index 145ddf0334..36ac26883d 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.UI/Dock/DockControl.xaml.cs
+++ b/src/modules/cmdpal/Microsoft.CmdPal.UI/Dock/DockControl.xaml.cs
@@ -11,7 +11,6 @@ using Microsoft.CmdPal.UI.ViewModels;
 using Microsoft.CmdPal.UI.ViewModels.Dock;
 using Microsoft.CmdPal.UI.ViewModels.Messages;
 using Microsoft.CmdPal.UI.ViewModels.Settings;
-using Microsoft.CommandPalette.Extensions;
 using Microsoft.UI;
 using Microsoft.UI.Xaml;
 using Microsoft.UI.Xaml.Controls;
@@ -262,22 +261,19 @@ public sealed partial class DockControl : UserControl, IRecipient<CloseContextMe
         try
         {
             // TODO! This is where we need to decide whether to open the command
-            // as a context menu or as a full page. 
+            // as a context menu or as a full page.
             //
             // It might be the case that we should just have like... a
             // PerformDockCommandMessage like PerformCommandMessage but with the
-            // context that we should be opening the command as a flyout. 
-
-            PerformCommandMessage m = new(command.Model);
-            m.WithAnimation = false;
-            m.TransientPage = true;
+            // context that we should be opening the command as a flyout.
+            var m = PerformCommandMessage.CreateFlyoutMessage(command.Model, pos);
             WeakReferenceMessenger.Default.Send(m);
 
-            var isPage = command.Model.Unsafe is not IInvokableCommand invokable;
-            if (isPage)
-            {
-                WeakReferenceMessenger.Default.Send<RequestShowPaletteAtMessage>(new(pos));
-            }
+            // var isPage = command.Model.Unsafe is not IInvokableCommand invokable;
+            // if (isPage)
+            // {
+            //     WeakReferenceMessenger.Default.Send<RequestShowPaletteAtMessage>(new(pos));
+            // }
         }
         catch (COMException e)
         {
diff --git a/src/modules/cmdpal/Microsoft.CmdPal.UI/MainWindow.xaml b/src/modules/cmdpal/Microsoft.CmdPal.UI/MainWindow.xaml
index 32329e17a0..00f9c9a49d 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.UI/MainWindow.xaml
+++ b/src/modules/cmdpal/Microsoft.CmdPal.UI/MainWindow.xaml
@@ -16,6 +16,29 @@
     Closed="MainWindow_Closed"
     mc:Ignorable="d">
     <Grid x:Name="RootElement">
+        <Grid.Resources>
+            <Style
+                x:Name="ContextMenuFlyoutStyle"
+                BasedOn="{StaticResource DefaultFlyoutPresenterStyle}"
+                TargetType="FlyoutPresenter">
+                <Style.Setters>
+                    <Setter Property="Margin" Value="0" />
+                    <Setter Property="Padding" Value="0" />
+                    <Setter Property="Background" Value="{ThemeResource DesktopAcrylicTransparentBrush}" />
+                    <Setter Property="BorderBrush" Value="{ThemeResource DividerStrokeColorDefaultBrush}" />
+                </Style.Setters>
+            </Style>
+
+            <!--  Backdrop requires ShouldConstrainToRootBounds="False"  -->
+            <Flyout
+                x:Name="ContextMenuFlyout"
+                FlyoutPresenterStyle="{StaticResource ContextMenuFlyoutStyle}"
+                Opened="ContextMenuFlyout_Opened"
+                ShouldConstrainToRootBounds="False"
+                SystemBackdrop="{ThemeResource AcrylicBackgroundFillColorDefaultBackdrop}">
+                <controls:ContextMenu x:Name="ContextMenuControl" />
+            </Flyout>
+        </Grid.Resources>
 
         <controls:BlurImageControl
             HorizontalAlignment="Stretch"
diff --git a/src/modules/cmdpal/Microsoft.CmdPal.UI/MainWindow.xaml.cs b/src/modules/cmdpal/Microsoft.CmdPal.UI/MainWindow.xaml.cs
index f7a7a314e7..4f6f2a84d1 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.UI/MainWindow.xaml.cs
+++ b/src/modules/cmdpal/Microsoft.CmdPal.UI/MainWindow.xaml.cs
@@ -28,12 +28,12 @@ using Microsoft.UI.Composition.SystemBackdrops;
 using Microsoft.UI.Input;
 using Microsoft.UI.Windowing;
 using Microsoft.UI.Xaml;
+using Microsoft.UI.Xaml.Controls.Primitives;
 using Microsoft.Windows.AppLifecycle;
 using Windows.ApplicationModel.Activation;
 using Windows.Foundation;
 using Windows.Graphics;
 using Windows.System;
-using Windows.UI;
 using Windows.UI.WindowManagement;
 using Windows.Win32;
 using Windows.Win32.Foundation;
@@ -58,6 +58,8 @@ public sealed partial class MainWindow : WindowEx,
     IRecipient<NavigationDepthMessage>,
     IRecipient<SearchQueryMessage>,
     IRecipient<ErrorOccurredMessage>,
+    IRecipient<ShowCommandInContextMenuMessage>,
+    IRecipient<CloseContextMenuMessage>,
     IRecipient<DragStartedMessage>,
     IRecipient<DragCompletedMessage>,
     IDisposable
@@ -142,6 +144,8 @@ public sealed partial class MainWindow : WindowEx,
         WeakReferenceMessenger.Default.Register<NavigationDepthMessage>(this);
         WeakReferenceMessenger.Default.Register<SearchQueryMessage>(this);
         WeakReferenceMessenger.Default.Register<ErrorOccurredMessage>(this);
+        WeakReferenceMessenger.Default.Register<ShowCommandInContextMenuMessage>(this);
+        WeakReferenceMessenger.Default.Register<CloseContextMenuMessage>(this);
         WeakReferenceMessenger.Default.Register<DragStartedMessage>(this);
         WeakReferenceMessenger.Default.Register<DragCompletedMessage>(this);
 
@@ -676,6 +680,41 @@ public sealed partial class MainWindow : WindowEx,
         _sessionErrorCount++;
     }
 
+    public void Receive(ShowCommandInContextMenuMessage message)
+    {
+        DispatcherQueue.TryEnqueue(() =>
+        {
+            ContextMenuControl.ViewModel.SelectedItem = message.Context;
+            ContextMenuFlyout.ShouldConstrainToRootBounds = false;
+            ContextMenuFlyout.ShowMode = FlyoutShowMode.Standard;
+            ContextMenuFlyout.ShowAt(RootElement);
+
+            // ContextMenuFlyout.ShowAt(
+            //    RootElement,
+            //    new FlyoutShowOptions()
+            //    {
+            //        ShowMode = FlyoutShowMode.Standard,
+            //        Position = message.Position,
+            //    });
+        });
+    }
+
+    public void Receive(CloseContextMenuMessage message)
+    {
+        DispatcherQueue.TryEnqueue(() =>
+        {
+            if (ContextMenuFlyout.IsOpen)
+            {
+                ContextMenuFlyout.Hide();
+            }
+        });
+    }
+
+    private void ContextMenuFlyout_Opened(object sender, object e)
+    {
+        ContextMenuControl.FocusSearchBox();
+    }
+
     /// <summary>
     /// Ends the current telemetry session and emits the CmdPal_SessionDuration event.
     /// Aggregates all session metrics collected since ShowWindow and sends them to telemetry.