Just like I drew it up

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

@@ -8,6 +8,7 @@ using Microsoft.CmdPal.Core.ViewModels;
 using Microsoft.CmdPal.Core.ViewModels.Models;
 using Microsoft.CmdPal.UI.ViewModels.Services;
 using Microsoft.CommandPalette.Extensions;
+using Microsoft.CommandPalette.Extensions.Toolkit;
 using Microsoft.Extensions.DependencyInjection;
 
 using Windows.Foundation;
@@ -153,6 +154,9 @@ public sealed class CommandProviderWrapper
             // On a BG thread here
             var fallbacks = model.FallbackCommands();
 
+            // Load pinned commands from saved settings
+            var pinnedCommands = LoadPinnedCommands(model, providerSettings);
+
             if (model is ICommandProvider2 two)
             {
                 UnsafePreCacheApiAdditions(two);
@@ -175,7 +179,7 @@ public sealed class CommandProviderWrapper
             Settings = new(model.Settings, this, _taskScheduler);
 
             // We do need to explicitly initialize commands though
-            InitializeCommands(commands, fallbacks, serviceProvider, pageContext);
+            InitializeCommands(commands, fallbacks, pinnedCommands, serviceProvider, pageContext);
 
             Logger.LogDebug($"Loaded commands from {DisplayName} ({ProviderId})");
         }
@@ -206,7 +210,7 @@ public sealed class CommandProviderWrapper
         }
     }
 
-    private void InitializeCommands(ICommandItem[] commands, IFallbackCommandItem[] fallbacks, IServiceProvider serviceProvider, WeakReference<IPageContext> pageContext)
+    private void InitializeCommands(ICommandItem[] commands, IFallbackCommandItem[] fallbacks, ICommandItem[] pinnedCommands, IServiceProvider serviceProvider, WeakReference<IPageContext> pageContext)
     {
         var settings = serviceProvider.GetService<SettingsModel>()!;
         var providerSettings = GetProviderSettings(settings);
@@ -220,13 +224,20 @@ public sealed class CommandProviderWrapper
             return topLevelViewModel;
         };
 
+        var topLevelList = new List<TopLevelViewModel>();
+
         if (commands is not null)
         {
-            TopLevelItems = commands
-                .Select(c => makeAndAdd(c, false))
-                .ToArray();
+            topLevelList.AddRange(commands.Select(c => makeAndAdd(c, false)));
         }
 
+        if (pinnedCommands is not null)
+        {
+            topLevelList.AddRange(pinnedCommands.Select(c => makeAndAdd(c, false)));
+        }
+
+        TopLevelItems = topLevelList.ToArray();
+
         if (fallbacks is not null)
         {
             FallbackItems = fallbacks
@@ -235,6 +246,32 @@ public sealed class CommandProviderWrapper
         }
     }
 
+    private ICommandItem[] LoadPinnedCommands(ICommandProvider model, ProviderSettings providerSettings)
+    {
+        var pinnedItems = new List<ICommandItem>();
+
+        if (model is ICommandProvider4 provider4)
+        {
+            foreach (var pinnedId in providerSettings.PinnedCommandIds)
+            {
+                try
+                {
+                    var commandItem = provider4.GetCommandItem(pinnedId);
+                    if (commandItem is not null)
+                    {
+                        pinnedItems.Add(commandItem);
+                    }
+                }
+                catch (Exception e)
+                {
+                    Logger.LogError($"Failed to load pinned command {pinnedId}: {e.Message}");
+                }
+            }
+        }
+
+        return pinnedItems.ToArray();
+    }
+
     private void UnsafePreCacheApiAdditions(ICommandProvider2 provider)
     {
         var apiExtensions = provider.GetApiExtensionStubs();
@@ -248,6 +285,21 @@ public sealed class CommandProviderWrapper
         }
     }
 
+    public void PinCommand(string commandId, IServiceProvider serviceProvider)
+    {
+        var settings = serviceProvider.GetService<SettingsModel>()!;
+        var providerSettings = GetProviderSettings(settings);
+
+        if (!providerSettings.PinnedCommandIds.Contains(commandId))
+        {
+            providerSettings.PinnedCommandIds.Add(commandId);
+            SettingsModel.SaveSettings(settings);
+
+            // Raise CommandsChanged so the TopLevelCommandManager reloads our commands
+            this.CommandsChanged?.Invoke(this, new ItemsChangedEventArgs(-1));
+        }
+    }
+
     public CommandProviderContext GetProviderContext()
     {
         return new() { ProviderId = ProviderId };

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

@@ -0,0 +1,9 @@
+// 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.
+
+namespace Microsoft.CmdPal.UI.ViewModels.Messages;
+
+public record PinCommandItemMessage(string ProviderId, string CommandId)
+{
+}

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

@@ -18,6 +18,8 @@ public class ProviderSettings
 
     public Dictionary<string, FallbackSettings> FallbackCommands { get; set; } = new();
 
+    public List<string> PinnedCommandIds { get; set; } = [];
+
     [JsonIgnore]
     public string ProviderDisplayName { get; set; } = string.Empty;
 

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

@@ -22,6 +22,7 @@ namespace Microsoft.CmdPal.UI.ViewModels;
 
 public partial class TopLevelCommandManager : ObservableObject,
     IRecipient<ReloadCommandsMessage>,
+    IRecipient<PinCommandItemMessage>,
     IPageContext,
     IDisposable
 {
@@ -42,6 +43,7 @@ public partial class TopLevelCommandManager : ObservableObject,
         _commandProviderCache = commandProviderCache;
         _taskScheduler = _serviceProvider.GetService<TaskScheduler>()!;
         WeakReferenceMessenger.Default.Register<ReloadCommandsMessage>(this);
+        WeakReferenceMessenger.Default.Register<PinCommandItemMessage>(this);
         _reloadCommandsGate = new(ReloadAllCommandsAsyncCore);
     }
 
@@ -414,6 +416,21 @@ public partial class TopLevelCommandManager : ObservableObject,
     public void Receive(ReloadCommandsMessage message) =>
         ReloadAllCommandsAsync().ConfigureAwait(false);
 
+    public void Receive(PinCommandItemMessage message)
+    {
+        var wrapper = LookupProvider(message.ProviderId);
+        wrapper?.PinCommand(message.CommandId, _serviceProvider);
+    }
+
+    private CommandProviderWrapper? LookupProvider(string providerId)
+    {
+        lock (_commandProvidersLock)
+        {
+            return _builtInCommands.FirstOrDefault(w => w.ProviderId == providerId)
+                   ?? _extensionCommandProviders.FirstOrDefault(w => w.ProviderId == providerId);
+        }
+    }
+
     void IPageContext.ShowException(Exception ex, string? extensionHint)
     {
         var message = DiagnosticsHelper.BuildExceptionMessage(ex, extensionHint ?? "TopLevelCommandManager");

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

@@ -27,7 +27,7 @@ public sealed partial class TopLevelViewModel : ObservableObject, IListItem, IEx
     private readonly IServiceProvider _serviceProvider;
     private readonly CommandItemViewModel _commandItemViewModel;
 
-    private readonly CommandProviderContext _commandProviderContext;
+    public CommandProviderContext ProviderContext { get; private set; }
 
     private string IdFromModel => IsFallback && !string.IsNullOrWhiteSpace(_fallbackId) ? _fallbackId : _commandItemViewModel.Command.Id;
 
@@ -57,7 +57,7 @@ public sealed partial class TopLevelViewModel : ObservableObject, IListItem, IEx
 
     public CommandItemViewModel ItemViewModel => _commandItemViewModel;
 
-    public string CommandProviderId => _commandProviderContext.ProviderId;
+    public string CommandProviderId => ProviderContext.ProviderId;
 
     ////// ICommandItem
     public string Title => _commandItemViewModel.Title;
@@ -199,7 +199,7 @@ public sealed partial class TopLevelViewModel : ObservableObject, IListItem, IEx
         _serviceProvider = serviceProvider;
         _settings = settings;
         _providerSettings = providerSettings;
-        _commandProviderContext = commandProviderContext;
+        ProviderContext = commandProviderContext;
         _commandItemViewModel = item;
 
         IsFallback = isFallback;

src/modules/cmdpal/Microsoft.CmdPal.UI/PowerToysAppHostService.cs

@@ -32,7 +32,7 @@ internal sealed class PowerToysAppHostService : IAppHostService
         CommandProviderContext? topLevelId = null;
         if (command is TopLevelViewModel topLevelViewModel)
         {
-            topLevelId = topLevelViewModel.CommandProviderContext;
+            topLevelId = topLevelViewModel.ProviderContext;
         }
 
         return topLevelId ?? currentContext ?? throw new InvalidOperationException("No command provider context could be found for the given command, and no current context was provided.");

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

@@ -6,7 +6,7 @@ using Windows.Foundation;
 
 namespace Microsoft.CommandPalette.Extensions.Toolkit;
 
-public abstract partial class CommandProvider : ICommandProvider, ICommandProvider2
+public abstract partial class CommandProvider : ICommandProvider, ICommandProvider2, ICommandProvider4
 {
     public virtual string Id { get; protected set; } = string.Empty;
 
@@ -22,6 +22,8 @@ public abstract partial class CommandProvider : ICommandProvider, ICommandProvid
 
     public virtual ICommand? GetCommand(string id) => null;
 
+    public virtual ICommandItem? GetCommandItem(string id) => null;
+
     public virtual ICommandSettings? Settings { get; protected set; }
 
     public virtual bool Frozen { get; protected set; } = true;

src/modules/cmdpal/extensionsdk/Microsoft.CommandPalette.Extensions/Microsoft.CommandPalette.Extensions.idl

@@ -405,6 +405,12 @@ namespace Microsoft.CommandPalette.Extensions
     {
         Object[] GetApiExtensionStubs();
     };
+
+    [contract(Microsoft.CommandPalette.Extensions.ExtensionsContract, 1)]
+    interface ICommandProvider4 requires ICommandProvider
+    {
+        ICommandItem GetCommandItem(String id);
+    };
     
 
 }