Add support for filterable, nested context menus (#38776)

_targets #38573_

At first I just wanted to add support for nested context menus.

But then I also had to add a search box, so the focus wouldn't get weird.

End result:

![nested-menus-001](https://github.com/user-attachments/assets/4e8f1ec8-4b09-4095-9b81-caf7abde8aea)

This gets rid of the need to have the search box and the command bar both track item keybindings - now it's just in the command bar.

Closes #38299
Closes #38442

src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/CommandBarViewModel.cs

@@ -4,18 +4,14 @@
 
 using System.Collections.ObjectModel;
 using CommunityToolkit.Mvvm.ComponentModel;
-using CommunityToolkit.Mvvm.Input;
 using CommunityToolkit.Mvvm.Messaging;
 using Microsoft.CmdPal.UI.ViewModels.Messages;
-using Microsoft.CommandPalette.Extensions;
-using Microsoft.CommandPalette.Extensions.Toolkit;
 using Windows.System;
 
 namespace Microsoft.CmdPal.UI.ViewModels;
 
 public partial class CommandBarViewModel : ObservableObject,
-    IRecipient<UpdateCommandBarMessage>,
-    IRecipient<UpdateItemKeybindingsMessage>
+    IRecipient<UpdateCommandBarMessage>
 {
     public ICommandBarContext? SelectedItem
     {
@@ -53,20 +49,17 @@ public partial class CommandBarViewModel : ObservableObject,
     public partial PageViewModel? CurrentPage { get; set; }
 
     [ObservableProperty]
-    public partial ObservableCollection<CommandContextItemViewModel> ContextCommands { get; set; } = [];
+    public partial ObservableCollection<ContextMenuStackViewModel> ContextMenuStack { get; set; } = [];
 
-    private Dictionary<KeyChord, CommandContextItemViewModel>? _contextKeybindings;
+    public ContextMenuStackViewModel? ContextMenu => ContextMenuStack.LastOrDefault();
 
     public CommandBarViewModel()
     {
         WeakReferenceMessenger.Default.Register<UpdateCommandBarMessage>(this);
-        WeakReferenceMessenger.Default.Register<UpdateItemKeybindingsMessage>(this);
     }
 
     public void Receive(UpdateCommandBarMessage message) => SelectedItem = message.ViewModel;
 
-    public void Receive(UpdateItemKeybindingsMessage message) => _contextKeybindings = message.Keys;
-
     private void SetSelectedItem(ICommandBarContext? value)
     {
         if (value != null)
@@ -111,7 +104,10 @@ public partial class CommandBarViewModel : ObservableObject,
         if (SelectedItem.MoreCommands.Count() > 1)
         {
             ShouldShowContextMenu = true;
-            ContextCommands = [.. SelectedItem.AllCommands.Where(c => c.ShouldBeVisible)];
+
+            ContextMenuStack.Clear();
+            ContextMenuStack.Add(new ContextMenuStackViewModel(SelectedItem));
+            OnPropertyChanged(nameof(ContextMenu));
         }
         else
         {
@@ -125,43 +121,80 @@ public partial class CommandBarViewModel : ObservableObject,
 
     // InvokeItemCommand is what this will be in Xaml due to source generator
     // this comes in when an item in the list is tapped
-    [RelayCommand]
-    private void InvokeItem(CommandContextItemViewModel item) =>
-       WeakReferenceMessenger.Default.Send<PerformCommandMessage>(new(item.Command.Model, item.Model));
+    // [RelayCommand]
+    public ContextKeybindingResult InvokeItem(CommandContextItemViewModel item) =>
+        PerformCommand(item);
 
     // this comes in when the primary button is tapped
     public void InvokePrimaryCommand()
     {
-        if (PrimaryCommand != null)
-        {
-            WeakReferenceMessenger.Default.Send<PerformCommandMessage>(new(PrimaryCommand.Command.Model, PrimaryCommand.Model));
-        }
+        PerformCommand(SecondaryCommand);
     }
 
     // this comes in when the secondary button is tapped
     public void InvokeSecondaryCommand()
     {
-        if (SecondaryCommand != null)
+        PerformCommand(SecondaryCommand);
+    }
+
+    public ContextKeybindingResult CheckKeybinding(bool ctrl, bool alt, bool shift, bool win, VirtualKey key)
+    {
+        var matchedItem = ContextMenu?.CheckKeybinding(ctrl, alt, shift, win, key);
+        return matchedItem != null ? PerformCommand(matchedItem) : ContextKeybindingResult.Unhandled;
+    }
+
+    private ContextKeybindingResult PerformCommand(CommandItemViewModel? command)
+    {
+        if (command == null)
         {
-            WeakReferenceMessenger.Default.Send<PerformCommandMessage>(new(SecondaryCommand.Command.Model, SecondaryCommand.Model));
+            return ContextKeybindingResult.Unhandled;
+        }
+
+        if (command.HasMoreCommands)
+        {
+            ContextMenuStack.Add(new ContextMenuStackViewModel(command));
+            OnPropertyChanging(nameof(ContextMenu));
+            OnPropertyChanged(nameof(ContextMenu));
+            return ContextKeybindingResult.KeepOpen;
+        }
+        else
+        {
+            WeakReferenceMessenger.Default.Send<PerformCommandMessage>(new(command.Command.Model, command.Model));
+            return ContextKeybindingResult.Hide;
         }
     }
 
-    public bool CheckKeybinding(bool ctrl, bool alt, bool shift, bool win, VirtualKey key)
+    public bool CanPopContextStack()
     {
-        if (_contextKeybindings != null)
+        return ContextMenuStack.Count > 1;
+    }
+
+    public void PopContextStack()
+    {
+        if (ContextMenuStack.Count > 1)
         {
-            // Does the pressed key match any of the keybindings?
-            var pressedKeyChord = KeyChordHelpers.FromModifiers(ctrl, alt, shift, win, key, 0);
-            if (_contextKeybindings.TryGetValue(pressedKeyChord, out var item))
-            {
-                // TODO GH #245: This is a bit of a hack, but we need to make sure that the keybindings are updated before we send the message
-                // so that the correct item is activated.
-                WeakReferenceMessenger.Default.Send<PerformCommandMessage>(new(item));
-                return true;
-            }
+            ContextMenuStack.RemoveAt(ContextMenuStack.Count - 1);
         }
 
-        return false;
+        OnPropertyChanging(nameof(ContextMenu));
+        OnPropertyChanged(nameof(ContextMenu));
+    }
+
+    public void ClearContextStack()
+    {
+        while (ContextMenuStack.Count > 1)
+        {
+            ContextMenuStack.RemoveAt(ContextMenuStack.Count - 1);
+        }
+
+        OnPropertyChanging(nameof(ContextMenu));
+        OnPropertyChanged(nameof(ContextMenu));
     }
 }
+
+public enum ContextKeybindingResult
+{
+    Unhandled,
+    Hide,
+    KeepOpen,
+}

src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/CommandItemViewModel.cs

@@ -48,7 +48,7 @@ public partial class CommandItemViewModel : ExtensionObjectViewModel, ICommandBa
 
     public List<CommandContextItemViewModel> MoreCommands { get; private set; } = [];
 
-    IEnumerable<CommandContextItemViewModel> ICommandBarContext.MoreCommands => MoreCommands;
+    IEnumerable<CommandContextItemViewModel> IContextMenuContext.MoreCommands => MoreCommands;
 
     public bool HasMoreCommands => MoreCommands.Count > 0;
 
@@ -187,23 +187,26 @@ public partial class CommandItemViewModel : ExtensionObjectViewModel, ICommandBa
         // use Initialize straight up
         MoreCommands.ForEach(contextItem =>
         {
-            contextItem.InitializeProperties();
+            contextItem.SlowInitializeProperties();
         });
 
-        _defaultCommandContextItem = new(new CommandContextItem(model.Command!), PageContext)
+        if (!string.IsNullOrEmpty(model.Command.Name))
         {
-            _itemTitle = Name,
-            Subtitle = Subtitle,
-            Command = Command,
+            _defaultCommandContextItem = new(new CommandContextItem(model.Command!), PageContext)
+            {
+                _itemTitle = Name,
+                Subtitle = Subtitle,
+                Command = Command,
 
-            // TODO this probably should just be a CommandContextItemViewModel(CommandItemViewModel) ctor, or a copy ctor or whatever
-        };
+                // TODO this probably should just be a CommandContextItemViewModel(CommandItemViewModel) ctor, or a copy ctor or whatever
+            };
 
-        // Only set the icon on the context item for us if our command didn't
-        // have its own icon
-        if (!Command.HasIcon)
-        {
-            _defaultCommandContextItem._listItemIcon = _listItemIcon;
+            // Only set the icon on the context item for us if our command didn't
+            // have its own icon
+            if (!Command.HasIcon)
+            {
+                _defaultCommandContextItem._listItemIcon = _listItemIcon;
+            }
         }
 
         Initialized |= InitializedState.SelectionInitialized;
@@ -398,23 +401,6 @@ public partial class CommandItemViewModel : ExtensionObjectViewModel, ICommandBa
         base.SafeCleanup();
         Initialized |= InitializedState.CleanedUp;
     }
-
-    /// <summary>
-    /// Generates a mapping of key -> command item for this particular item's
-    /// MoreCommands. (This won't include the primary Command, but it will
-    /// include the secondary one). This map can be used to quickly check if a
-    /// shortcut key was pressed
-    /// </summary>
-    /// <returns>a dictionary of KeyChord -> Context commands, for all commands
-    /// that have a shortcut key set.</returns>
-    internal Dictionary<KeyChord, CommandContextItemViewModel> Keybindings()
-    {
-        return MoreCommands
-            .Where(c => c.HasRequestedShortcut)
-            .ToDictionary(
-            c => c.RequestedShortcut ?? new KeyChord(0, 0, 0),
-            c => c);
-    }
 }
 
 [Flags]

src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/ContextMenuStackViewModel.cs

@@ -0,0 +1,82 @@
+// 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 System.Collections.ObjectModel;
+using CommunityToolkit.Mvvm.ComponentModel;
+using Microsoft.CmdPal.UI.ViewModels.Messages;
+using Microsoft.CommandPalette.Extensions.Toolkit;
+using Windows.System;
+
+namespace Microsoft.CmdPal.UI.ViewModels;
+
+public partial class ContextMenuStackViewModel : ObservableObject
+{
+    [ObservableProperty]
+    public partial ObservableCollection<CommandContextItemViewModel> FilteredItems { get; set; }
+
+    private readonly IContextMenuContext _context;
+    private string _lastSearchText = string.Empty;
+
+    // private Dictionary<KeyChord, CommandContextItemViewModel>? _contextKeybindings;
+    public ContextMenuStackViewModel(IContextMenuContext context)
+    {
+        _context = context;
+        FilteredItems = [.. context.AllCommands];
+    }
+
+    public void SetSearchText(string searchText)
+    {
+        if (searchText == _lastSearchText)
+        {
+            return;
+        }
+
+        _lastSearchText = searchText;
+
+        var commands = _context.AllCommands.Where(c => c.ShouldBeVisible);
+        if (string.IsNullOrEmpty(searchText))
+        {
+            ListHelpers.InPlaceUpdateList(FilteredItems, commands);
+            return;
+        }
+
+        var newResults = ListHelpers.FilterList<CommandContextItemViewModel>(commands, searchText, ScoreContextCommand);
+        ListHelpers.InPlaceUpdateList(FilteredItems, newResults);
+    }
+
+    private static int ScoreContextCommand(string query, CommandContextItemViewModel item)
+    {
+        if (string.IsNullOrEmpty(query) || string.IsNullOrWhiteSpace(query))
+        {
+            return 1;
+        }
+
+        if (string.IsNullOrEmpty(item.Title))
+        {
+            return 0;
+        }
+
+        var nameMatch = StringMatcher.FuzzySearch(query, item.Title);
+
+        var descriptionMatch = StringMatcher.FuzzySearch(query, item.Subtitle);
+
+        return new[] { nameMatch.Score, (descriptionMatch.Score - 4) / 2, 0 }.Max();
+    }
+
+    public CommandContextItemViewModel? CheckKeybinding(bool ctrl, bool alt, bool shift, bool win, VirtualKey key)
+    {
+        var keybindings = _context.Keybindings();
+        if (keybindings != null)
+        {
+            // Does the pressed key match any of the keybindings?
+            var pressedKeyChord = KeyChordHelpers.FromModifiers(ctrl, alt, shift, win, key, 0);
+            if (keybindings.TryGetValue(pressedKeyChord, out var item))
+            {
+                return item;
+            }
+        }
+
+        return null;
+    }
+}

src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/ListViewModel.cs

@@ -344,8 +344,6 @@ public partial class ListViewModel : PageViewModel, IDisposable
            {
                WeakReferenceMessenger.Default.Send<UpdateCommandBarMessage>(new(item));
 
-               WeakReferenceMessenger.Default.Send<UpdateItemKeybindingsMessage>(new(item.Keybindings()));
-
                if (ShowDetails && item.HasDetails)
                {
                    WeakReferenceMessenger.Default.Send<ShowDetailsMessage>(new(item.Details));

src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Messages/TryCommandKeybindingMessage.cs

@@ -2,8 +2,11 @@
 // 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.CommandPalette.Extensions;
+using Windows.System;
 
 namespace Microsoft.CmdPal.UI.ViewModels.Messages;
 
-public record UpdateItemKeybindingsMessage(Dictionary<KeyChord, CommandContextItemViewModel>? Keys);
+public record TryCommandKeybindingMessage(bool Ctrl, bool Alt, bool Shift, bool Win, VirtualKey Key)
+{
+    public bool Handled { get; set; }
+}

src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Messages/UpdateCommandBarMessage.cs

@@ -3,6 +3,7 @@
 // See the LICENSE file in the project root for more information.
 
 using System.ComponentModel;
+using Microsoft.CommandPalette.Extensions;
 
 namespace Microsoft.CmdPal.UI.ViewModels.Messages;
 
@@ -13,22 +14,42 @@ public record UpdateCommandBarMessage(ICommandBarContext? ViewModel)
 {
 }
 
-// Represents everything the command bar needs to know about to show command
-// buttons at the bottom.
-//
-// This is implemented by both ListItemViewModel and ContentPageViewModel,
-// the two things with sub-commands.
-public interface ICommandBarContext : INotifyPropertyChanged
+public interface IContextMenuContext : INotifyPropertyChanged
 {
     public IEnumerable<CommandContextItemViewModel> MoreCommands { get; }
 
     public bool HasMoreCommands { get; }
 
+    public List<CommandContextItemViewModel> AllCommands { get; }
+
+    /// <summary>
+    /// Generates a mapping of key -> command item for this particular item's
+    /// MoreCommands. (This won't include the primary Command, but it will
+    /// include the secondary one). This map can be used to quickly check if a
+    /// shortcut key was pressed
+    /// </summary>
+    /// <returns>a dictionary of KeyChord -> Context commands, for all commands
+    /// that have a shortcut key set.</returns>
+    public Dictionary<KeyChord, CommandContextItemViewModel> Keybindings()
+    {
+        return MoreCommands
+            .Where(c => c.HasRequestedShortcut)
+            .ToDictionary(
+            c => c.RequestedShortcut ?? new KeyChord(0, 0, 0),
+            c => c);
+    }
+}
+
+// Represents everything the command bar needs to know about to show command
+// buttons at the bottom.
+//
+// This is implemented by both ListItemViewModel and ContentPageViewModel,
+// the two things with sub-commands.
+public interface ICommandBarContext : IContextMenuContext
+{
     public string SecondaryCommandName { get; }
 
     public CommandItemViewModel? PrimaryCommand { get; }
 
     public CommandItemViewModel? SecondaryCommand { get; }
-
-    public List<CommandContextItemViewModel> AllCommands { get; }
 }

src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/CommandBar.xaml

@@ -225,27 +225,42 @@
                 ToolTipService.ToolTip="Ctrl+K"
                 Visibility="{x:Bind ViewModel.ShouldShowContextMenu, Mode=OneWay}">
                 <Button.Flyout>
-                    <Flyout Placement="TopEdgeAlignedRight">
-                        <ListView
-                            x:Name="CommandsDropdown"
-                            MinWidth="248"
-                            Margin="-16,-12,-16,-12"
-                            IsItemClickEnabled="True"
-                            ItemClick="CommandsDropdown_ItemClick"
-                            ItemTemplate="{StaticResource ContextMenuViewModelTemplate}"
-                            ItemsSource="{x:Bind ViewModel.ContextCommands, Mode=OneWay}"
-                            KeyDown="CommandsDropdown_KeyDown"
-                            SelectionMode="None">
-                            <ListView.ItemContainerStyle>
-                                <Style BasedOn="{StaticResource DefaultListViewItemStyle}" TargetType="ListViewItem">
-                                    <Setter Property="MinHeight" Value="0" />
-                                    <Setter Property="Padding" Value="12,7,12,7" />
-                                </Style>
-                            </ListView.ItemContainerStyle>
-                            <ListView.ItemContainerTransitions>
-                                <TransitionCollection />
-                            </ListView.ItemContainerTransitions>
-                        </ListView>
+                    <Flyout
+                        Closing="Flyout_Closing"
+                        Opened="Flyout_Opened"
+                        Placement="TopEdgeAlignedRight">
+                        <StackPanel>
+
+                            <ListView
+                                x:Name="CommandsDropdown"
+                                MinWidth="248"
+                                Margin="-16,-12,-16,-12"
+                                IsItemClickEnabled="True"
+                                ItemClick="CommandsDropdown_ItemClick"
+                                ItemTemplate="{StaticResource ContextMenuViewModelTemplate}"
+                                ItemsSource="{x:Bind ViewModel.ContextMenu.FilteredItems, Mode=OneWay}"
+                                KeyDown="CommandsDropdown_KeyDown"
+                                SelectionMode="Single">
+                                <ListView.ItemContainerStyle>
+                                    <Style BasedOn="{StaticResource DefaultListViewItemStyle}" TargetType="ListViewItem">
+                                        <Setter Property="MinHeight" Value="0" />
+                                        <Setter Property="Padding" Value="12,7,12,7" />
+                                    </Style>
+                                </ListView.ItemContainerStyle>
+                                <ListView.ItemContainerTransitions>
+                                    <TransitionCollection />
+                                </ListView.ItemContainerTransitions>
+                            </ListView>
+
+                            <TextBox
+                                x:Name="ContextFilterBox"
+                                x:Uid="ContextFilterBox"
+                                Margin="-12,12,-12,-12"
+                                KeyDown="ContextFilterBox_KeyDown"
+                                PreviewKeyDown="ContextFilterBox_PreviewKeyDown"
+                                TextChanged="ContextFilterBox_TextChanged" />
+
+                        </StackPanel>
                     </Flyout>
                 </Button.Flyout>
             </Button>

src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/CommandBar.xaml.cs

@@ -18,9 +18,10 @@ namespace Microsoft.CmdPal.UI.Controls;
 
 public sealed partial class CommandBar : UserControl,
     IRecipient<OpenContextMenuMessage>,
+    IRecipient<TryCommandKeybindingMessage>,
     ICurrentPageAware
 {
-    public CommandBarViewModel ViewModel { get; set; } = new();
+    public CommandBarViewModel ViewModel { get; } = new();
 
     public PageViewModel? CurrentPageViewModel
     {
@@ -38,6 +39,9 @@ public sealed partial class CommandBar : UserControl,
 
         // RegisterAll isn't AOT compatible
         WeakReferenceMessenger.Default.Register<OpenContextMenuMessage>(this);
+        WeakReferenceMessenger.Default.Register<TryCommandKeybindingMessage>(this);
+
+        ViewModel.PropertyChanged += ViewModel_PropertyChanged;
     }
 
     public void Receive(OpenContextMenuMessage message)
@@ -52,8 +56,41 @@ public sealed partial class CommandBar : UserControl,
             ShowMode = FlyoutShowMode.Standard,
         };
         MoreCommandsButton.Flyout.ShowAt(MoreCommandsButton, options);
-        CommandsDropdown.SelectedIndex = 0;
-        CommandsDropdown.Focus(FocusState.Programmatic);
+        UpdateUiForStackChange();
+    }
+
+    public void Receive(TryCommandKeybindingMessage msg)
+    {
+        if (!ViewModel.ShouldShowContextMenu)
+        {
+            return;
+        }
+
+        var result = ViewModel?.CheckKeybinding(msg.Ctrl, msg.Alt, msg.Shift, msg.Win, msg.Key);
+
+        if (result == ContextKeybindingResult.Hide)
+        {
+            msg.Handled = true;
+        }
+        else if (result == ContextKeybindingResult.KeepOpen)
+        {
+            if (!MoreCommandsButton.Flyout.IsOpen)
+            {
+                var options = new FlyoutShowOptions
+                {
+                    ShowMode = FlyoutShowMode.Standard,
+                };
+                MoreCommandsButton.Flyout.ShowAt(MoreCommandsButton, options);
+            }
+
+            UpdateUiForStackChange();
+
+            msg.Handled = true;
+        }
+        else if (result == ContextKeybindingResult.Unhandled)
+        {
+            msg.Handled = false;
+        }
     }
 
     [System.Diagnostics.CodeAnalysis.SuppressMessage("CodeQuality", "IDE0051:Remove unused private members", Justification = "VS has a tendency to delete XAML bound methods over-aggressively")]
@@ -88,8 +125,14 @@ public sealed partial class CommandBar : UserControl,
     {
         if (e.ClickedItem is CommandContextItemViewModel item)
         {
-            ViewModel?.InvokeItemCommand.Execute(item);
-            MoreCommandsButton.Flyout.Hide();
+            if (ViewModel?.InvokeItem(item) == ContextKeybindingResult.Hide)
+            {
+                MoreCommandsButton.Flyout.Hide();
+            }
+            else
+            {
+                UpdateUiForStackChange();
+            }
         }
     }
 
@@ -106,9 +149,136 @@ public sealed partial class CommandBar : UserControl,
         var winPressed = InputKeyboardSource.GetKeyStateForCurrentThread(VirtualKey.LeftWindows).HasFlag(CoreVirtualKeyStates.Down) ||
             InputKeyboardSource.GetKeyStateForCurrentThread(VirtualKey.RightWindows).HasFlag(CoreVirtualKeyStates.Down);
 
-        if (ViewModel?.CheckKeybinding(ctrlPressed, altPressed, shiftPressed, winPressed, e.Key) ?? false)
+        var result = ViewModel?.CheckKeybinding(ctrlPressed, altPressed, shiftPressed, winPressed, e.Key);
+
+        if (result == ContextKeybindingResult.Hide)
+        {
+            e.Handled = true;
+            MoreCommandsButton.Flyout.Hide();
+            WeakReferenceMessenger.Default.Send<FocusSearchBoxMessage>();
+        }
+        else if (result == ContextKeybindingResult.KeepOpen)
         {
             e.Handled = true;
         }
+        else if (result == ContextKeybindingResult.Unhandled)
+        {
+            e.Handled = false;
+        }
+    }
+
+    private void Flyout_Opened(object sender, object e)
+    {
+        UpdateUiForStackChange();
+    }
+
+    private void Flyout_Closing(FlyoutBase sender, FlyoutBaseClosingEventArgs args)
+    {
+        ViewModel?.ClearContextStack();
+        WeakReferenceMessenger.Default.Send<FocusSearchBoxMessage>();
+    }
+
+    private void ViewModel_PropertyChanged(object? sender, System.ComponentModel.PropertyChangedEventArgs e)
+    {
+        var prop = e.PropertyName;
+        if (prop == nameof(ViewModel.ContextMenu))
+        {
+            UpdateUiForStackChange();
+        }
+    }
+
+    private void ContextFilterBox_TextChanged(object sender, TextChangedEventArgs e)
+    {
+        ViewModel.ContextMenu?.SetSearchText(ContextFilterBox.Text);
+
+        if (CommandsDropdown.SelectedIndex == -1)
+        {
+            CommandsDropdown.SelectedIndex = 0;
+        }
+    }
+
+    private void ContextFilterBox_KeyDown(object sender, KeyRoutedEventArgs e)
+    {
+        var ctrlPressed = InputKeyboardSource.GetKeyStateForCurrentThread(VirtualKey.Control).HasFlag(CoreVirtualKeyStates.Down);
+        var altPressed = InputKeyboardSource.GetKeyStateForCurrentThread(VirtualKey.Menu).HasFlag(CoreVirtualKeyStates.Down);
+        var shiftPressed = InputKeyboardSource.GetKeyStateForCurrentThread(VirtualKey.Shift).HasFlag(CoreVirtualKeyStates.Down);
+        var winPressed = InputKeyboardSource.GetKeyStateForCurrentThread(VirtualKey.LeftWindows).HasFlag(CoreVirtualKeyStates.Down) ||
+            InputKeyboardSource.GetKeyStateForCurrentThread(VirtualKey.RightWindows).HasFlag(CoreVirtualKeyStates.Down);
+
+        if (e.Key == VirtualKey.Enter)
+        {
+            if (CommandsDropdown.SelectedItem is CommandContextItemViewModel item)
+            {
+                if (ViewModel?.InvokeItem(item) == ContextKeybindingResult.Hide)
+                {
+                    MoreCommandsButton.Flyout.Hide();
+                    WeakReferenceMessenger.Default.Send<FocusSearchBoxMessage>();
+                }
+                else
+                {
+                    UpdateUiForStackChange();
+                }
+
+                e.Handled = true;
+            }
+        }
+        else if (e.Key == VirtualKey.Escape ||
+            (e.Key == VirtualKey.Left && altPressed))
+        {
+            if (ViewModel.CanPopContextStack())
+            {
+                ViewModel.PopContextStack();
+                UpdateUiForStackChange();
+            }
+            else
+            {
+                MoreCommandsButton.Flyout.Hide();
+                WeakReferenceMessenger.Default.Send<FocusSearchBoxMessage>();
+            }
+
+            e.Handled = true;
+        }
+
+        CommandsDropdown_KeyDown(sender, e);
+    }
+
+    private void ContextFilterBox_PreviewKeyDown(object sender, KeyRoutedEventArgs e)
+    {
+        if (e.Key == VirtualKey.Up)
+        {
+            // navigate previous
+            if (CommandsDropdown.SelectedIndex > 0)
+            {
+                CommandsDropdown.SelectedIndex--;
+            }
+            else
+            {
+                CommandsDropdown.SelectedIndex = CommandsDropdown.Items.Count - 1;
+            }
+
+            e.Handled = true;
+        }
+        else if (e.Key == VirtualKey.Down)
+        {
+            // navigate next
+            if (CommandsDropdown.SelectedIndex < CommandsDropdown.Items.Count - 1)
+            {
+                CommandsDropdown.SelectedIndex++;
+            }
+            else
+            {
+                CommandsDropdown.SelectedIndex = 0;
+            }
+
+            e.Handled = true;
+        }
+    }
+
+    private void UpdateUiForStackChange()
+    {
+        ContextFilterBox.Text = string.Empty;
+        ViewModel.ContextMenu?.SetSearchText(string.Empty);
+        CommandsDropdown.SelectedIndex = 0;
+        ContextFilterBox.Focus(FocusState.Programmatic);
     }
 }

src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/SearchBar.xaml.cs

@@ -8,8 +8,6 @@ using CommunityToolkit.WinUI;
 using Microsoft.CmdPal.UI.ViewModels;
 using Microsoft.CmdPal.UI.ViewModels.Messages;
 using Microsoft.CmdPal.UI.Views;
-using Microsoft.CommandPalette.Extensions;
-using Microsoft.CommandPalette.Extensions.Toolkit;
 using Microsoft.UI.Dispatching;
 using Microsoft.UI.Input;
 using Microsoft.UI.Xaml;
@@ -23,7 +21,6 @@ namespace Microsoft.CmdPal.UI.Controls;
 public sealed partial class SearchBar : UserControl,
     IRecipient<GoHomeMessage>,
     IRecipient<FocusSearchBoxMessage>,
-    IRecipient<UpdateItemKeybindingsMessage>,
     ICurrentPageAware
 {
     private readonly DispatcherQueue _queue = DispatcherQueue.GetForCurrentThread();
@@ -34,8 +31,6 @@ public sealed partial class SearchBar : UserControl,
     private readonly DispatcherQueueTimer _debounceTimer = DispatcherQueue.GetForCurrentThread().CreateTimer();
     private bool _isBackspaceHeld;
 
-    private Dictionary<KeyChord, CommandContextItemViewModel>? _keyBindings;
-
     public PageViewModel? CurrentPageViewModel
     {
         get => (PageViewModel?)GetValue(CurrentPageViewModelProperty);
@@ -74,7 +69,6 @@ public sealed partial class SearchBar : UserControl,
         this.InitializeComponent();
         WeakReferenceMessenger.Default.Register<GoHomeMessage>(this);
         WeakReferenceMessenger.Default.Register<FocusSearchBoxMessage>(this);
-        WeakReferenceMessenger.Default.Register<UpdateItemKeybindingsMessage>(this);
     }
 
     public void ClearSearch()
@@ -173,17 +167,14 @@ public sealed partial class SearchBar : UserControl,
             WeakReferenceMessenger.Default.Send<NavigateBackMessage>(new());
         }
 
-        if (_keyBindings != null)
+        if (!e.Handled)
         {
-            // Does the pressed key match any of the keybindings?
-            var pressedKeyChord = KeyChordHelpers.FromModifiers(ctrlPressed, altPressed, shiftPressed, winPressed, (int)e.Key, 0);
-            if (_keyBindings.TryGetValue(pressedKeyChord, out var item))
-            {
-                // TODO GH #245: This is a bit of a hack, but we need to make sure that the keybindings are updated before we send the message
-                // so that the correct item is activated.
-                WeakReferenceMessenger.Default.Send<PerformCommandMessage>(new(item));
-                e.Handled = true;
-            }
+            // The CommandBar is responsible for handling all the item keybindings,
+            // since the bound context item may need to then show another
+            // context menu
+            TryCommandKeybindingMessage msg = new(ctrlPressed, altPressed, shiftPressed, winPressed, e.Key);
+            WeakReferenceMessenger.Default.Send(msg);
+            e.Handled = msg.Handled;
         }
     }
 
@@ -302,10 +293,5 @@ public sealed partial class SearchBar : UserControl,
 
     public void Receive(GoHomeMessage message) => ClearSearch();
 
-    public void Receive(FocusSearchBoxMessage message) => this.Focus(Microsoft.UI.Xaml.FocusState.Programmatic);
-
-    public void Receive(UpdateItemKeybindingsMessage message)
-    {
-        _keyBindings = message.Keys;
-    }
+    public void Receive(FocusSearchBoxMessage message) => FilterBox.Focus(Microsoft.UI.Xaml.FocusState.Programmatic);
 }

src/modules/cmdpal/Microsoft.CmdPal.UI/Pages/ShellPage.xaml.cs

@@ -187,8 +187,6 @@ public sealed partial class ShellPage : Microsoft.UI.Xaml.Controls.Page,
 
                     WeakReferenceMessenger.Default.Send<UpdateCommandBarMessage>(new(null));
 
-                    WeakReferenceMessenger.Default.Send<UpdateItemKeybindingsMessage>(new(null));
-
                     var isMainPage = command is MainListPage;
 
                     // Construct our ViewModel of the appropriate type and pass it the UI Thread context.

src/modules/cmdpal/Microsoft.CmdPal.UI/Strings/en-us/Resources.resw

@@ -394,6 +394,9 @@ Right-click to remove the key combination, thereby deactivating the shortcut.</v
   <data name="BehaviorSettingsHeader.Text" xml:space="preserve">
     <value>Behavior</value>
   </data>
+  <data name="ContextFilterBox.PlaceholderText" xml:space="preserve">
+    <value>Search commands...</value>
+  </data>
   <data name="Settings_GeneralPage_ShowSystemTrayIcon_SettingsCard.Header" xml:space="preserve">
     <value>Show system tray icon</value>
   </data>

src/modules/cmdpal/ext/SamplePagesExtension/EvilSamplesPage.cs

@@ -6,6 +6,7 @@ using System.Threading;
 using System.Threading.Tasks;
 using Microsoft.CommandPalette.Extensions;
 using Microsoft.CommandPalette.Extensions.Toolkit;
+using Windows.System;
 
 namespace SamplePagesExtension;
 
@@ -76,7 +77,136 @@ public partial class EvilSamplesPage : ListPage
            {
                Body = "This is a test for GH#512. If it doesn't appear immediately, it's likely InvokeCommand is happening on the UI thread.",
            },
-        }
+        },
+
+        // More edge cases than truly evil
+        new ListItem(
+            new ToastCommand("Primary command invoked", MessageState.Info) { Name = "Primary command", Icon = new IconInfo("\uF146") }) // dial 1
+        {
+            Title = "anonymous command test",
+            Subtitle = "Try pressing Ctrl+1 with me selected",
+            Icon = new IconInfo("\uE712"),  // "More" dots
+            MoreCommands = [
+                new CommandContextItem(
+                    new ToastCommand("Secondary command invoked", MessageState.Warning) { Name = "Secondary command", Icon = new IconInfo("\uF147") }) // dial 2
+                {
+                    Title = "I'm a second command",
+                    RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.Number1),
+                },
+                new CommandContextItem("nested...")
+                {
+                    Title = "We can go deeper...",
+                    Icon = new IconInfo("\uF148"),
+                    RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.Number2),
+                    MoreCommands = [
+                        new CommandContextItem(
+                            new ToastCommand("Nested A invoked") { Name = "Do it", Icon = new IconInfo("A") })
+                        {
+                            Title = "Nested A",
+                            RequestedShortcut = KeyChordHelpers.FromModifiers(alt: true, vkey: VirtualKey.A),
+                        },
+
+                        new CommandContextItem(
+                            new ToastCommand("Nested B invoked") { Name = "Do it", Icon = new IconInfo("B") })
+                        {
+                            Title = "Nested B...",
+                            RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.B),
+                            MoreCommands = [
+                                new CommandContextItem(
+                                    new ToastCommand("Nested C invoked") { Name = "Do it" })
+                                {
+                                    Title = "You get it",
+                                    RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.B),
+                                }
+                            ],
+                        },
+                    ],
+                }
+            ],
+        },
+        new ListItem(
+            new ToastCommand("Primary command invoked", MessageState.Info) { Name = "Primary command", Icon = new IconInfo("\uF146") }) // dial 1
+        {
+            Title = "noop command test",
+            Subtitle = "Try pressing Ctrl+1 with me selected",
+            Icon = new IconInfo("\uE712"),  // "More" dots
+            MoreCommands = [
+                new CommandContextItem(
+                    new ToastCommand("Secondary command invoked", MessageState.Warning) { Name = "Secondary command", Icon = new IconInfo("\uF147") }) // dial 2
+                {
+                    Title = "I'm a second command",
+                    RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.Number1),
+                },
+                new CommandContextItem(new NoOpCommand())
+                {
+                    Title = "We can go deeper...",
+                    Icon = new IconInfo("\uF148"),
+                    RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.Number2),
+                    MoreCommands = [
+                        new CommandContextItem(
+                            new ToastCommand("Nested A invoked") { Name = "Do it", Icon = new IconInfo("A") })
+                        {
+                            Title = "Nested A",
+                            RequestedShortcut = KeyChordHelpers.FromModifiers(alt: true, vkey: VirtualKey.A),
+                        },
+
+                        new CommandContextItem(
+                            new ToastCommand("Nested B invoked") { Name = "Do it", Icon = new IconInfo("B") })
+                        {
+                            Title = "Nested B...",
+                            RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.B),
+                            MoreCommands = [
+                                new CommandContextItem(
+                                    new ToastCommand("Nested C invoked") { Name = "Do it" })
+                                {
+                                    Title = "You get it",
+                                    RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.B),
+                                }
+                            ],
+                        },
+                    ],
+                }
+            ],
+        },
+        new ListItem(
+            new ToastCommand("Primary command invoked", MessageState.Info) { Name = "Primary command", Icon = new IconInfo("\uF146") }) // dial 1
+        {
+            Title = "noop secondary command test",
+            Subtitle = "Try pressing Ctrl+1 with me selected",
+            Icon = new IconInfo("\uE712"),  // "More" dots
+            MoreCommands = [
+                new CommandContextItem(new NoOpCommand())
+                {
+                    Title = "We can go deeper...",
+                    Icon = new IconInfo("\uF148"),
+                    RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.Number2),
+                    MoreCommands = [
+                        new CommandContextItem(
+                            new ToastCommand("Nested A invoked") { Name = "Do it", Icon = new IconInfo("A") })
+                        {
+                            Title = "Nested A",
+                            RequestedShortcut = KeyChordHelpers.FromModifiers(alt: true, vkey: VirtualKey.A),
+                        },
+
+                        new CommandContextItem(
+                            new ToastCommand("Nested B invoked") { Name = "Do it", Icon = new IconInfo("B") })
+                        {
+                            Title = "Nested B...",
+                            RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.B),
+                            MoreCommands = [
+                                new CommandContextItem(
+                                    new ToastCommand("Nested C invoked") { Name = "Do it" })
+                                {
+                                    Title = "You get it",
+                                    RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.B),
+                                }
+                            ],
+                        },
+                    ],
+                }
+            ],
+        },
+
     ];
 
     public EvilSamplesPage()

src/modules/cmdpal/ext/SamplePagesExtension/Pages/SampleListPage.cs

@@ -69,62 +69,47 @@ internal sealed partial class SampleListPage : ListPage
             },
 
             new ListItem(
-                new AnonymousCommand(() =>
-                {
-                    var t = new ToastStatusMessage(new StatusMessage()
-                    {
-                        Message = "Primary command invoked",
-                        State = MessageState.Info,
-                    });
-                    t.Show();
-                })
-                {
-                    Result = CommandResult.KeepOpen(),
-                    Icon = new IconInfo("\uE712"),
-                })
+                new ToastCommand("Primary command invoked", MessageState.Info) { Name = "Primary command", Icon = new IconInfo("\uF146") }) // dial 1
             {
                 Title = "You can add context menu items too. Press Ctrl+k",
                 Subtitle = "Try pressing Ctrl+1 with me selected",
-                Icon = new IconInfo("\uE712"),
+                Icon = new IconInfo("\uE712"),  // "More" dots
                 MoreCommands = [
                     new CommandContextItem(
-                        new AnonymousCommand(() =>
-                        {
-                            var t = new ToastStatusMessage(new StatusMessage()
-                            {
-                                Message = "Secondary command invoked",
-                                State = MessageState.Warning,
-                            });
-                            t.Show();
-                        })
-                        {
-                            Name = "Secondary command",
-                            Icon = new IconInfo("\uF147"), // Dial 2
-                            Result = CommandResult.KeepOpen(),
-                        })
+                        new ToastCommand("Secondary command invoked", MessageState.Warning) { Name = "Secondary command", Icon = new IconInfo("\uF147") }) // dial 2
                     {
                         Title = "I'm a second command",
                         RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.Number1),
                     },
                     new CommandContextItem(
-                        new AnonymousCommand(() =>
-                        {
-                            var t = new ToastStatusMessage(new StatusMessage()
-                            {
-                                Message = "Third command invoked",
-                                State = MessageState.Error,
-                            });
-                            t.Show();
-                        })
-                        {
-                            Name = "Do it",
-                            Icon = new IconInfo("\uF148"), // dial 3
-                            Result = CommandResult.KeepOpen(),
-                        })
+                        new ToastCommand("Third command invoked", MessageState.Error) { Name = "Do 3", Icon = new IconInfo("\uF148") }) // dial 3
                     {
-                        Title = "A third command too",
+                        Title = "We can go deeper...",
                         Icon = new IconInfo("\uF148"),
                         RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.Number2),
+                        MoreCommands = [
+                            new CommandContextItem(
+                                new ToastCommand("Nested A invoked") { Name = "Do it", Icon = new IconInfo("A") })
+                            {
+                                Title = "Nested A",
+                                RequestedShortcut = KeyChordHelpers.FromModifiers(alt: true, vkey: VirtualKey.A),
+                            },
+
+                            new CommandContextItem(
+                                new ToastCommand("Nested B invoked") { Name = "Do it", Icon = new IconInfo("B") })
+                            {
+                                Title = "Nested B...",
+                                RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.B),
+                                MoreCommands = [
+                                    new CommandContextItem(
+                                        new ToastCommand("Nested C invoked") { Name = "Do it" })
+                                    {
+                                        Title = "You get it",
+                                        RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, vkey: VirtualKey.B),
+                                    }
+                                ],
+                            },
+                        ],
                     }
                 ],
             },
@@ -183,7 +168,6 @@ internal sealed partial class SampleListPage : ListPage
             {
                 Title = "Get the name of the Foreground window",
             },
-
         ];
     }
 }

src/modules/cmdpal/ext/SamplePagesExtension/Pages/ToastCommand.cs

@@ -0,0 +1,23 @@
+// 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.CommandPalette.Extensions;
+using Microsoft.CommandPalette.Extensions.Toolkit;
+
+namespace SamplePagesExtension;
+
+internal sealed partial class ToastCommand(string message, MessageState state = MessageState.Info) : InvokableCommand
+{
+    public override ICommandResult Invoke()
+    {
+        var t = new ToastStatusMessage(new StatusMessage()
+        {
+            Message = message,
+            State = state,
+        });
+        t.Show();
+
+        return CommandResult.KeepOpen();
+    }
+}

src/modules/cmdpal/extensionsdk/Microsoft.CommandPalette.Extensions.Toolkit/ListItem.cs

@@ -61,4 +61,9 @@ public partial class ListItem : CommandItem, IListItem
         : base(command)
     {
     }
+
+    public ListItem()
+        : base()
+    {
+    }
 }