add logs

## Summary of the Pull Request
A new Third-Party plugin to search on Perplexity

---------

Co-authored-by: Mike Griese <migrie@microsoft.com>
Co-authored-by: Heiko <61519853+htcfreek@users.noreply.github.com>
Co-authored-by: Kayla Cinnamon <cinnamon@microsoft.com>

.github/actions/spell-check/allow/code.txt

@@ -94,6 +94,7 @@ onefuzzingestionpreparationtool
 OTP
 Yubi
 Yubico
+Perplexity
 svgl
 
 # KEYS

.github/actions/spell-check/allow/names.txt

@@ -29,6 +29,8 @@ shortcutguide
 
 # 8LWXpg is user name but user folder causes a flag
 LWXpg
+# 0x6f677548 is user name but user folder causes a flag
+x6f677548
 Adoumie
 Advaith
 alekhyareddy

.github/actions/spell-check/expect.txt

@@ -306,6 +306,7 @@ CXVIRTUALSCREEN
 CYSCREEN
 CYSMICON
 CYVIRTUALSCREEN
+Czechia
 cziplib
 Dac
 dacl
@@ -330,6 +331,7 @@ Deact
 debugbreak
 decryptor
 Dedup
+Deduplicator
 Deeplink
 DEFAULTBOOTSTRAPPERINSTALLFOLDER
 DEFAULTCOLOR
@@ -435,6 +437,7 @@ EDITSHORTCUTS
 EDITTEXT
 EFile
 ekus
+emojis
 ENABLEDELAYEDEXPANSION
 ENABLEDPOPUP
 ENABLETAB
@@ -799,6 +802,7 @@ KEYBOARDMANAGEREDITORLIBRARYWRAPPER
 keyboardmanagerstate
 keyboardmanagerui
 keyboardtester
+keycap
 KEYEVENTF
 KEYIMAGE
 keynum
@@ -1780,10 +1784,13 @@ UACUI
 UAL
 uap
 UBR
+UBreak
+ubrk
 UCallback
 ucrt
 ucrtd
 uefi
+UError
 uesc
 UFlags
 UHash
@@ -1853,6 +1860,7 @@ VFT
 vget
 vgetq
 viewmodels
+virama
 VIRTKEY
 VIRTUALDESK
 VISEGRADRELAY

.github/workflows/manual-batch-issue-deduplication.yml

@@ -1,20 +1,38 @@
 name: Manual Batch Issue Deduplication
 
 on:
-  workflow_dispatch: # Only runs when manually triggered
+  workflow_dispatch:
+    inputs:
+      issue_numbers:
+        description: "JSON array of issue numbers to deduplicate (e.g. [101,102,103])"
+        required: true
+      since:
+        description: "Only compare against issues created after this date (ISO 8601, e.g. 2019-05-05T00:00:00Z)"
+        required: false
+        default: "2019-05-05T00:00:00Z"
+      label_as_duplicate:
+        description: "Apply duplicate label if duplicates are found (true/false)"
+        required: false
+        default: "true"
+
+permissions:
+  models: read
+  issues: write
 
 jobs:
-  batch-deduplicate:
+  deduplicate:
     runs-on: ubuntu-latest
+    strategy:
+      matrix:
+        issue: ${{ fromJson(github.event.inputs.issue_numbers) }}
     steps:
-      - name: Batch Deduplicate Issues
+      - name: Checkout
+        uses: actions/checkout@v3
+
+      - name: Run GenAI Issue Deduplicator
         uses: pelikhan/action-genai-issue-dedup@v0
         with:
-          github-token: ${{ secrets.GITHUB_TOKEN }}
-          label-duplicate: "potential duplicate"
-          comment-duplicate: true
-          close-duplicate: false
-          batch-size: 100 
-          since: '2019-05-05T00:00:00Z' # Process issues dating back to 2019
-          duplicate-comment-template: "This issue appears to be a duplicate of #{duplicate_issue_number}."
-          # Add other action-specific inputs if needed
+          github_token: ${{ secrets.GITHUB_TOKEN }}
+          github_issue: ${{ matrix.issue }}
+          label_as_duplicate: ${{ github.event.inputs.label_as_duplicate }}
+          

doc/thirdPartyRunPlugins.md

@@ -73,4 +73,5 @@ Below are community created plugins that target a website or software.  They are
 | [YubicoOauthOTP](https://github.com/dlnilsson/Community.PowerToys.Run.Plugin.YubicoOauthOTP) | [dlnilsson](https://github.com/dlnilsson) | Display generated codes from OATH accounts stored on the YubiKey in powerToys Run  |
 | [Firefox Bookmark](https://github.com/8LWXpg/PowerToysRun-FirefoxBookmark) | [8LWXpg](https://github.com/8LWXpg) | Open bookmarks in Firefox based browser |
 | [Linear](https://github.com/vednig/powertoys-linear) | [vednig](https://github.com/vednig) | Create Linear Issues directly from Powertoys Run |
+| [PerplexitySearchShortcut](https://github.com/0x6f677548/PowerToys-Run-PerplexitySearchShortcut) | [0x6f677548](https://github.com/0x6f677548) | Search Perplexity |
 | [SpeedTest](https://github.com/ruslanlap/PowerToysRun-SpeedTest) | [ruslanlap](https://github.com/ruslanlap) | One-command internet speed tests with real-time results, modern UI, and shareable links. |

src/common/UITestAutomation/UITestBase.cs

@@ -4,6 +4,7 @@
 
 using System.Collections.ObjectModel;
 using System.Diagnostics;
+using System.IO;
 using System.Runtime.InteropServices;
 using System.Text.RegularExpressions;
 using Microsoft.VisualStudio.TestTools.UnitTesting;
@@ -94,6 +95,7 @@ namespace Microsoft.PowerToys.UITest
                 {
                     Task.Delay(1000).Wait();
                     AddScreenShotsToTestResultsDirectory();
+                    AddLogFilesToTestResultsDirectory();
                 }
             }
 
@@ -598,6 +600,92 @@ namespace Microsoft.PowerToys.UITest
             }
         }
 
+        /// <summary>
+        /// Copies PowerToys log files to test results directory when test fails.
+        /// Renames files to include the directory structure after \PowerToys.
+        /// </summary>
+        protected void AddLogFilesToTestResultsDirectory()
+        {
+            try
+            {
+                var localAppDataLow = Path.Combine(
+                    Environment.GetEnvironmentVariable("USERPROFILE") ?? string.Empty,
+                    "AppData",
+                    "LocalLow",
+                    "Microsoft",
+                    "PowerToys");
+
+                if (Directory.Exists(localAppDataLow))
+                {
+                    CopyLogFilesFromDirectory(localAppDataLow, string.Empty);
+                }
+
+                var localAppData = Path.Combine(
+                    Environment.GetEnvironmentVariable("LOCALAPPDATA") ?? string.Empty,
+                    "Microsoft",
+                    "PowerToys");
+
+                if (Directory.Exists(localAppData))
+                {
+                    CopyLogFilesFromDirectory(localAppData, string.Empty);
+                }
+            }
+            catch (Exception ex)
+            {
+                // Don't fail the test if log file copying fails
+                Console.WriteLine($"Failed to copy log files: {ex.Message}");
+            }
+        }
+
+        /// <summary>
+        /// Recursively copies log files from a directory and renames them with directory structure.
+        /// </summary>
+        /// <param name="sourceDir">Source directory to copy from</param>
+        /// <param name="relativePath">Relative path from PowerToys folder</param>
+        private void CopyLogFilesFromDirectory(string sourceDir, string relativePath)
+        {
+            if (!Directory.Exists(sourceDir))
+            {
+                return;
+            }
+
+            // Process log files in current directory
+            var logFiles = Directory.GetFiles(sourceDir, "*.log");
+            foreach (var logFile in logFiles)
+            {
+                try
+                {
+                    var fileName = Path.GetFileName(logFile);
+                    var fileNameWithoutExt = Path.GetFileNameWithoutExtension(fileName);
+                    var extension = Path.GetExtension(fileName);
+
+                    // Create new filename with directory structure
+                    var directoryPart = string.IsNullOrEmpty(relativePath) ? string.Empty : relativePath.Replace("\\", "-") + "-";
+                    var newFileName = $"{directoryPart}{fileNameWithoutExt}{extension}";
+
+                    // Copy file to test results directory with new name
+                    var testResultsDir = TestContext.TestResultsDirectory ?? Path.GetTempPath();
+                    var destinationPath = Path.Combine(testResultsDir, newFileName);
+
+                    File.Copy(logFile, destinationPath, true);
+                    TestContext.AddResultFile(destinationPath);
+                }
+                catch (Exception ex)
+                {
+                    Console.WriteLine($"Failed to copy log file {logFile}: {ex.Message}");
+                }
+            }
+
+            // Recursively process subdirectories
+            var subdirectories = Directory.GetDirectories(sourceDir);
+            foreach (var subdir in subdirectories)
+            {
+                var dirName = Path.GetFileName(subdir);
+                var newRelativePath = string.IsNullOrEmpty(relativePath) ? dirName : Path.Combine(relativePath, dirName);
+                CopyLogFilesFromDirectory(subdir, newRelativePath);
+            }
+        }
+
         /// <summary>
         /// Restart scope exe.
         /// </summary>

src/modules/cmdpal/Microsoft.CmdPal.Common/Commands/ConfirmableCommand.cs

@@ -0,0 +1,155 @@
+// 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;
+using System.Diagnostics.CodeAnalysis;
+using Microsoft.CommandPalette.Extensions;
+using Microsoft.CommandPalette.Extensions.Toolkit;
+
+namespace Microsoft.CmdPal.Common.Commands;
+
+public sealed partial class ConfirmableCommand : InvokableCommand
+{
+    private readonly IInvokableCommand? _command;
+
+    public Func<bool>? IsConfirmationRequired { get; init; }
+
+    public required string ConfirmationTitle { get; init; }
+
+    public required string ConfirmationMessage { get; init; }
+
+    public required IInvokableCommand Command
+    {
+        get => _command!;
+        init
+        {
+            if (_command is INotifyPropChanged oldNotifier)
+            {
+                oldNotifier.PropChanged -= InnerCommand_PropChanged;
+            }
+
+            _command = value;
+
+            if (_command is INotifyPropChanged notifier)
+            {
+                notifier.PropChanged += InnerCommand_PropChanged;
+            }
+
+            OnPropertyChanged(nameof(Name));
+            OnPropertyChanged(nameof(Id));
+            OnPropertyChanged(nameof(Icon));
+        }
+    }
+
+    public override string Name
+    {
+        get => (_command as Command)?.Name ?? base.Name;
+        set
+        {
+            if (_command is Command cmd)
+            {
+                cmd.Name = value;
+            }
+            else
+            {
+                base.Name = value;
+            }
+        }
+    }
+
+    public override string Id
+    {
+        get => (_command as Command)?.Id ?? base.Id;
+        set
+        {
+            var previous = Id;
+            if (_command is Command cmd)
+            {
+                cmd.Id = value;
+            }
+            else
+            {
+                base.Id = value;
+            }
+
+            if (previous != Id)
+            {
+                OnPropertyChanged(nameof(Id));
+            }
+        }
+    }
+
+    public override IconInfo Icon
+    {
+        get => (_command as Command)?.Icon ?? base.Icon;
+        set
+        {
+            if (_command is Command cmd)
+            {
+                cmd.Icon = value;
+            }
+            else
+            {
+                base.Icon = value;
+            }
+        }
+    }
+
+    public ConfirmableCommand()
+    {
+        // Allow init-only construction
+    }
+
+    [SetsRequiredMembers]
+    public ConfirmableCommand(IInvokableCommand command, string confirmationTitle, string confirmationMessage, Func<bool>? isConfirmationRequired = null)
+    {
+        ArgumentNullException.ThrowIfNull(command);
+        ArgumentException.ThrowIfNullOrWhiteSpace(confirmationMessage);
+        ArgumentNullException.ThrowIfNull(confirmationMessage);
+
+        IsConfirmationRequired = isConfirmationRequired;
+        ConfirmationTitle = confirmationTitle;
+        ConfirmationMessage = confirmationMessage;
+        Command = command;
+    }
+
+    private void InnerCommand_PropChanged(object sender, IPropChangedEventArgs args)
+    {
+        var property = args.PropertyName;
+
+        if (string.IsNullOrEmpty(property) || property == nameof(Name))
+        {
+            OnPropertyChanged(nameof(Name));
+        }
+
+        if (string.IsNullOrEmpty(property) || property == nameof(Id))
+        {
+            OnPropertyChanged(nameof(Id));
+        }
+
+        if (string.IsNullOrEmpty(property) || property == nameof(Icon))
+        {
+            OnPropertyChanged(nameof(Icon));
+        }
+    }
+
+    public override ICommandResult Invoke()
+    {
+        var showConfirmationDialog = IsConfirmationRequired?.Invoke() ?? true;
+        if (showConfirmationDialog)
+        {
+            return CommandResult.Confirm(new ConfirmationArgs
+            {
+                Title = ConfirmationTitle,
+                Description = ConfirmationMessage,
+                PrimaryCommand = Command,
+                IsPrimaryCommandCritical = true,
+            });
+        }
+        else
+        {
+            return Command.Invoke(this) ?? CommandResult.Dismiss();
+        }
+    }
+}

src/modules/cmdpal/Microsoft.CmdPal.Common/Helpers/WellKnownKeyChords.cs

@@ -0,0 +1,51 @@
+// 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;
+
+using Windows.System;
+
+namespace Microsoft.CmdPal.Common.Helpers;
+
+/// <summary>
+/// Well-known key chords used in the Command Palette and extensions.
+/// </summary>
+/// <remarks>
+/// Assigned key chords should not conflict with system or application shortcuts.
+/// However, the key chords in this class are not guaranteed to be unique and may conflict
+/// with each other, especially when commands appear together in the same menu.
+/// </remarks>
+public static class WellKnownKeyChords
+{
+    /// <summary>
+    /// Gets the well-known key chord for opening the file location. Shortcut: Ctrl+Shift+E.
+    /// </summary>
+    public static KeyChord OpenFileLocation { get; } = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: (int)VirtualKey.E);
+
+    /// <summary>
+    /// Gets the well-known key chord for copying the file path. Shortcut: Ctrl+Shift+C.
+    /// </summary>
+    public static KeyChord CopyFilePath { get; } = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: (int)VirtualKey.C);
+
+    /// <summary>
+    /// Gets the well-known key chord for opening the current location in a console. Shortcut: Ctrl+Shift+R.
+    /// </summary>
+    public static KeyChord OpenInConsole { get; } = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: (int)VirtualKey.R);
+
+    /// <summary>
+    /// Gets the well-known key chord for running the selected item as administrator. Shortcut: Ctrl+Shift+Enter.
+    /// </summary>
+    public static KeyChord RunAsAdministrator { get; } = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: (int)VirtualKey.Enter);
+
+    /// <summary>
+    /// Gets the well-known key chord for running the selected item as a different user. Shortcut: Ctrl+Shift+U.
+    /// </summary>
+    public static KeyChord RunAsDifferentUser { get; } = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: (int)VirtualKey.U);
+
+    /// <summary>
+    /// Gets the well-known key chord for toggling the pin state. Shortcut: Ctrl+P.
+    /// </summary>
+    public static KeyChord TogglePin { get; } = KeyChordHelpers.FromModifiers(ctrl: true, vkey: (int)VirtualKey.P);
+}

src/modules/cmdpal/Microsoft.CmdPal.UI/Controls/IconBox.cs

@@ -2,8 +2,10 @@
 // The Microsoft Corporation licenses this file to you under the MIT license.
 // See the LICENSE file in the project root for more information.
 
+using ManagedCommon;
 using Microsoft.CmdPal.Core.ViewModels;
 using Microsoft.CmdPal.UI.Deferred;
+using Microsoft.Terminal.UI;
 using Microsoft.UI.Dispatching;
 using Microsoft.UI.Xaml;
 using Microsoft.UI.Xaml.Controls;
@@ -55,6 +57,8 @@ public partial class IconBox : ContentControl
     {
         TabFocusNavigation = KeyboardNavigationMode.Once;
         IsTabStop = false;
+        HorizontalContentAlignment = HorizontalAlignment.Center;
+        VerticalContentAlignment = VerticalAlignment.Center;
     }
 
     private static void OnSourcePropertyChanged(DependencyObject d, DependencyPropertyChangedEventArgs e)
@@ -75,6 +79,8 @@ public partial class IconBox : ContentControl
                     IconSourceElement elem = new()
                     {
                         IconSource = fontIco,
+                        HorizontalAlignment = HorizontalAlignment.Center,
+                        VerticalAlignment = VerticalAlignment.Center,
                     };
                     @this.Content = elem;
                     break;
@@ -98,14 +104,20 @@ public partial class IconBox : ContentControl
             else
             {
                 // TODO GH #239 switch back when using the new MD text block
+                // Switching back to EnqueueAsync has broken icons in tags (they don't show)
                 // _ = @this._queue.EnqueueAsync(() =>
-                @this._queue.TryEnqueue(new(async () =>
+                @this._queue.TryEnqueue(async void () =>
                 {
-                    var requestedTheme = @this.ActualTheme;
-                    var eventArgs = new SourceRequestedEventArgs(e.NewValue, requestedTheme);
-
-                    if (@this.SourceRequested is not null)
+                    try
                     {
+                        if (@this.SourceRequested is null)
+                        {
+                            return;
+                        }
+
+                        var requestedTheme = @this.ActualTheme;
+                        var eventArgs = new SourceRequestedEventArgs(e.NewValue, requestedTheme);
+
                         await @this.SourceRequested.InvokeAsync(@this, eventArgs);
 
                         // After the await:
@@ -130,37 +142,35 @@ public partial class IconBox : ContentControl
                         // So, if the icon we get back was a font icon,
                         // and the glyph for that icon is NOT in the range of
                         // Segoe icons, then let's give the icon some extra space
-                        @this.Padding = new Thickness(0);
-
-                        IconDataViewModel? iconData = null;
-                        if (eventArgs.Key is IconDataViewModel)
+                        var iconData = eventArgs.Key switch
                         {
-                            iconData = eventArgs.Key as IconDataViewModel;
+                            IconDataViewModel key => key,
+                            IconInfoViewModel info => requestedTheme == ElementTheme.Light ? info.Light : info.Dark,
+                            _ => null,
+                        };
+
+                        if (iconData?.Icon is not null && @this.Source is FontIconSource)
+                        {
+                            var iconSize =
+                                !double.IsNaN(@this.Width) ? @this.Width :
+                                !double.IsNaN(@this.Height) ? @this.Height :
+                                @this.ActualWidth > 0 ? @this.ActualWidth :
+                                @this.ActualHeight;
+
+                            @this.Padding = new Thickness(Math.Round(iconSize * -0.2));
                         }
-                        else if (eventArgs.Key is IconInfoViewModel info)
+                        else
                         {
-                            iconData = requestedTheme == ElementTheme.Light ? info.Light : info.Dark;
-                        }
-
-                        if (iconData is not null &&
-                            @this.Source is FontIconSource)
-                        {
-                            if (!string.IsNullOrEmpty(iconData.Icon) && iconData.Icon.Length <= 2)
-                            {
-                                var ch = iconData.Icon[0];
-
-                                // The range of MDL2 Icons isn't explicitly defined, but
-                                // we're using this based off the table on:
-                                // https://docs.microsoft.com/en-us/windows/uwp/design/style/segoe-ui-symbol-font
-                                var isMDL2Icon = ch is >= '\uE700' and <= '\uF8FF';
-                                if (!isMDL2Icon)
-                                {
-                                    @this.Padding = new Thickness(-4);
-                                }
-                            }
+                            @this.Padding = default;
                         }
                     }
-                }));
+                    catch (Exception ex)
+                    {
+                        // Exception from TryEnqueue bypasses the global error handler,
+                        // and crashes the app.
+                        Logger.LogError("Failed to set icon", ex);
+                    }
+                });
             }
         }
     }

src/modules/cmdpal/Microsoft.Terminal.UI/FontIconGlyphClassifier.cpp

@@ -0,0 +1,177 @@
+#include "pch.h"
+#include "FontIconGlyphClassifier.h"
+#include "FontIconGlyphClassifier.g.cpp"
+
+#include <icu.h>
+#include <utility>
+
+namespace winrt::Microsoft::Terminal::UI::implementation
+{
+    namespace
+    {
+        // Check if the code point is in the Private Use Area range used by Fluent UI icons.
+        [[nodiscard]] constexpr bool _isFluentIconPua(const UChar32 cp) noexcept
+        {
+            static constexpr UChar32 _fluentIconsPrivateUseAreaStart = 0xE700;
+            static constexpr UChar32 _fluentIconsPrivateUseAreaEnd = 0xF8FF;
+            return cp >= _fluentIconsPrivateUseAreaStart && cp <= _fluentIconsPrivateUseAreaEnd;
+        }
+
+        // Determine if the given text (as a sequence of UChar code units) is emoji
+        [[nodiscard]] bool _isEmoji(const UChar* p, const int32_t length) noexcept
+        {
+            if (!p || length < 1)
+            {
+                return false;
+            }
+
+            // https://www.unicode.org/reports/tr51/#Emoji_Variation_Selector_Notes
+            constexpr UChar32 vs15CodePoint = 0xFE0E; // Variation Selectors 15: text variation selector
+            constexpr UChar32 vs16CodePoint = 0xFE0F; // Variation Selectors: 16 emoji variation selector
+
+            // Decode the first code point correctly (surrogate-safe)
+            int32_t i0{ 0 };
+            UChar32 first{ 0 };
+            U16_NEXT(p, i0, length, first);
+
+            for (int32_t i = 0; i < length;)
+            {
+                UChar32 cp{ 0 };
+                U16_NEXT(p, i, length, cp);
+
+                if (cp == vs16CodePoint) { return true; }
+                if (cp == vs15CodePoint) { return false; }
+            }
+
+            return !U_IS_SURROGATE(first) && u_hasBinaryProperty(first, UCHAR_EMOJI_PRESENTATION);
+        }
+    }
+
+    bool FontIconGlyphClassifier::IsLikelyToBeEmojiOrSymbolIcon(const hstring& text)
+    {
+        if (text.empty())
+        {
+            return false;
+        }
+
+        if (text.size() == 1 && !IS_HIGH_SURROGATE(text[0]))
+        {
+            // If it's a single code unit, it's definitely either zero or one grapheme clusters.
+            // If it turns out to be illegal Unicode, we don't really care.
+            return true;
+        }
+
+        if (text.size() >= 2 && text[0] <= 0x7F && text[1] <= 0x7F)
+        {
+            // Two adjacent ASCII characters (as seen in most file paths) aren't a single
+            // grapheme cluster.
+            return false;
+        }
+
+        // Use ICU to determine whether text is composed of a single grapheme cluster.
+        int32_t off{ 0 };
+        UErrorCode status{ U_ZERO_ERROR };
+
+        UBreakIterator* const bi{ ubrk_open(UBRK_CHARACTER,
+                                            nullptr,
+                                            reinterpret_cast<const UChar*>(text.data()),
+                                            static_cast<int>(text.size()),
+                                            &status) };
+        if (bi)
+        {
+            if (U_SUCCESS(status))
+            {
+                off = ubrk_next(bi);
+            }
+            ubrk_close(bi);
+        }
+        return std::cmp_equal(off, text.size());
+    }
+
+    FontIconGlyphKind FontIconGlyphClassifier::Classify(hstring const& text) noexcept
+    {
+        if (text.empty())
+        {
+            return FontIconGlyphKind::None;
+        }
+
+        const size_t textSize{ text.size() };
+        const auto* buffer{ reinterpret_cast<const UChar*>(text.c_str()) };
+
+        // Fast path 1: Single UTF-16 code unit (most common case)
+        if (textSize == 1)
+        {
+            const UChar ch{ buffer[0] };
+
+            if (IS_HIGH_SURROGATE(ch))
+            {
+                return FontIconGlyphKind::Invalid;
+            }
+
+            if (_isFluentIconPua(ch))
+            {
+                return FontIconGlyphKind::FluentSymbol;
+            }
+
+            if (_isEmoji(&ch, 1))
+            {
+                return FontIconGlyphKind::Emoji;
+            }
+
+            return FontIconGlyphKind::Other;
+        }
+
+        // Fast path 2: Common file path pattern - two ASCII printable characters
+        if (textSize >= 2 && buffer[0] <= 0x7F && buffer[1] <= 0x7F)
+        {
+            // Definitely multiple graphemes
+            return FontIconGlyphKind::Invalid;
+        }
+
+        // Expensive path: Use ICU to determine grapheme boundaries
+        UErrorCode status{ U_ZERO_ERROR };
+
+        UBreakIterator* bi{ ubrk_open(UBRK_CHARACTER,
+                                      nullptr,
+                                      buffer,
+                                      static_cast<int32_t>(textSize),
+                                      &status) };
+
+        if (U_FAILURE(status) || !bi)
+        {
+            return FontIconGlyphKind::Invalid;
+        }
+
+        const int32_t start{ ubrk_first(bi) };
+        const int32_t end{ ubrk_next(bi) }; // end of first grapheme
+        ubrk_close(bi);
+
+        // No graphemes found
+        if (end == UBRK_DONE || end <= start)
+        {
+            return FontIconGlyphKind::None;
+        }
+
+        // If there's more than one grapheme, it's not a valid icon glyph
+        if (std::cmp_not_equal(end, textSize))
+        {
+            return FontIconGlyphKind::Invalid;
+        }
+
+        // Exactly one grapheme: classify
+        const UChar* grapheme = buffer + start;
+        const int32_t graphemeLength = end - start;
+
+        if (graphemeLength == 1 && _isFluentIconPua(grapheme[0]))
+        {
+            return FontIconGlyphKind::FluentSymbol;
+        }
+
+        if (_isEmoji(grapheme, graphemeLength))
+        {
+            return FontIconGlyphKind::Emoji;
+        }
+
+        return FontIconGlyphKind::Other;
+    }
+}

src/modules/cmdpal/Microsoft.Terminal.UI/FontIconGlyphClassifier.h

@@ -0,0 +1,18 @@
+#pragma once
+
+#include "FontIconGlyphClassifier.g.h"
+
+namespace winrt::Microsoft::Terminal::UI::implementation
+{
+    struct FontIconGlyphClassifier
+    {
+        [[nodiscard]] static bool IsLikelyToBeEmojiOrSymbolIcon(const winrt::hstring& text);
+
+        [[nodiscard]] static FontIconGlyphKind Classify(winrt::hstring const& text) noexcept;
+    };
+}
+
+namespace winrt::Microsoft::Terminal::UI::factory_implementation
+{
+    BASIC_FACTORY(FontIconGlyphClassifier);
+}

src/modules/cmdpal/Microsoft.Terminal.UI/FontIconGlyphClassifier.idl

@@ -0,0 +1,62 @@
+// Copyright (c) Microsoft Corporation.
+// Licensed under the MIT license.
+
+namespace Microsoft.Terminal.UI
+{
+    /// <summary>
+    /// Categorizes the type of a single grapheme cluster or input text.
+    /// Used to determine how the input should be handled or rendered (for example,
+    /// whether it should be treated as an emoji, an icon from a symbol font, plain text, etc.).
+    /// </summary>
+    enum FontIconGlyphKind
+    {
+        /// <summary>
+        /// Input is invalid or contains more than one grapheme cluster and therefore cannot be
+        /// treated as a single symbol. Typical for multi-character text like file paths
+        /// or composed strings that include separators.
+        /// </summary>
+        Invalid = -1,
+
+        /// <summary>
+        /// No grapheme present (empty string). Indicates absence of a symbol.
+        /// </summary>
+        None = 0,
+
+        /// <summary>
+        /// A single emoji grapheme cluster. This may consist of multiple Unicode code
+        /// points combined into one visible glyph (e.g., emoji with modifiers or ZWJ sequences).
+        /// </summary>
+        Emoji = 1,
+
+        /// <summary>
+        /// A single glyph from the Segoe Fluent Icons / MDL2 Assets Private Use Area (PUA),
+        /// typically in the Unicode range U+E700–U+F8FF. These are font-based icons (Fluent/MDL2).
+        /// </summary>
+        FluentSymbol = 2,
+
+        /// <summary>
+        /// A single non-emoji grapheme that is not a Fluent/MDL2 PUA symbol.
+        /// Covers ordinary characters, letters, numbers, or other single glyph symbols.
+        /// </summary>
+        Other = 3,
+    };
+
+    /// <summary>
+    /// Static utility class for text and icon analysis
+    /// </summary>
+    static runtimeclass FontIconGlyphClassifier
+    {
+        /// <summary>
+        /// Determines if text represents a single grapheme cluster (emoji/symbol icon).
+        /// Uses ICU for Unicode boundary detection to distinguish icons from file paths.
+        /// </summary>
+        /// <param name="text">Text to analyze</param>
+        /// <returns>True if single grapheme cluster, false for multi-character text or paths</returns>
+        static Boolean IsLikelyToBeEmojiOrSymbolIcon(String text);
+
+        /// <summary>
+        /// Classifies the input into a glyph kind suitable for icon or text rendering.
+        /// </summary>
+        static FontIconGlyphKind Classify(String text);
+    };
+}

src/modules/cmdpal/Microsoft.Terminal.UI/IconPathConverter.cpp

@@ -2,7 +2,7 @@
 #include "IconPathConverter.h"
 #include "IconPathConverter.g.cpp"
 
-// #include "Utils.h"
+ #include "FontIconGlyphClassifier.h"
 
 #include <Shlobj.h>
 #include <Shlobj_core.h>
@@ -110,7 +110,7 @@ namespace winrt::Microsoft::Terminal::UI::implementation
                 if (til::equals_insensitive_ascii(iconUri.Extension(), L".svg"))
                 {
                     typename ImageIconSource<TIconSource>::type iconSource;
-                    winrt::Microsoft::UI::Xaml::Media::Imaging::SvgImageSource source{ iconUri };	
+                    winrt::Microsoft::UI::Xaml::Media::Imaging::SvgImageSource source{ iconUri };
                     iconSource.ImageSource(source);
                     return iconSource;
                 }
@@ -169,41 +169,46 @@ namespace winrt::Microsoft::Terminal::UI::implementation
 
             // If we fail to set the icon source using the "icon" as a path,
             // let's try it as a symbol/emoji.
-            //
-            // Anything longer than 2 wchar_t's _isn't_ an emoji or symbol, so
-            // don't do this if it's just an invalid path.
-            if (!iconSource && iconPath.size() <= 2)
+            if (!iconSource)
             {
                 try
                 {
-                    typename FontIconSource<TIconSource>::type icon;
-                    const auto ch = til::at(iconPath, 0);
+                    const auto glyph_kind = FontIconGlyphClassifier::Classify(iconPath);
 
-                    // The range of MDL2 Icons isn't explicitly defined, but
-                    // we're using this based off the table on:
-                    // https://docs.microsoft.com/en-us/windows/uwp/design/style/segoe-ui-symbol-font
-                    const auto isMDL2Icon = ch >= L'\uE700' && ch <= L'\uF8FF';
-                    if (isMDL2Icon)
+                    winrt::hstring family;
+                    if (glyph_kind == FontIconGlyphKind::Invalid)
                     {
-                        icon.FontFamily(winrt::Microsoft::UI::Xaml::Media::FontFamily{ L"Segoe Fluent Icons, Segoe MDL2 Assets" });
+                        family = L"Segoe UI";
                     }
                     else if (!fontFamily.empty())
                     {
-                        icon.FontFamily(winrt::Microsoft::UI::Xaml::Media::FontFamily{ fontFamily });
-
+                        family = fontFamily;
+                    }
+                    else if (glyph_kind == FontIconGlyphKind::FluentSymbol)
+                    {
+                        family = L"Segoe Fluent Icons, Segoe MDL2 Assets";
+                    }
+                    else if (glyph_kind == FontIconGlyphKind::Emoji)
+                    {
+                        // Emoji and other symbols go in the Segoe UI Emoji font.
+                        // Some emojis (e.g. 2️⃣) would be rendered as emoji glyphs otherwise.
+                        family = L"Segoe UI Emoji, Segoe UI";
                     }
                     else
                     {
-                        // Note: you _do_ need to manually set the font here.
-                        icon.FontFamily(winrt::Microsoft::UI::Xaml::Media::FontFamily{ L"Segoe UI" });
+                        family = L"Segoe UI";
                     }
+
+                    typename FontIconSource<TIconSource>::type icon;
+                    icon.FontFamily(winrt::Microsoft::UI::Xaml::Media::FontFamily{ family });
                     icon.FontSize(targetSize);
-                    icon.Glyph(iconPath);
+                    icon.Glyph(glyph_kind == FontIconGlyphKind::Invalid ? L"\u25CC" : iconPath);
                     iconSource = icon;
                 }
                 CATCH_LOG();
             }
         }
+
         if (!iconSource)
         {
             // Set the default IconSource to a BitmapIconSource with a null source
@@ -326,7 +331,7 @@ namespace winrt::Microsoft::Terminal::UI::implementation
     }
 
     static winrt::Microsoft::UI::Xaml::Media::Imaging::SoftwareBitmapSource _getImageIconSourceForBinary(std::wstring_view iconPathWithoutIndex,
-                                                                                                         int index, 
+                                                                                                         int index,
                                                                                                          int targetSize)
     {
         // Try:

src/modules/cmdpal/Microsoft.Terminal.UI/Microsoft.Terminal.UI.vcxproj

@@ -159,6 +159,9 @@
     <ClInclude Include="ResourceString.h">
       <DependentUpon>ResourceString.idl</DependentUpon>
     </ClInclude>
+    <ClInclude Include="FontIconGlyphClassifier.h">
+      <DependentUpon>FontIconGlyphClassifier.idl</DependentUpon>
+    </ClInclude>
   </ItemGroup>
   <ItemGroup>
     <ClCompile Include="init.cpp" />
@@ -178,6 +181,9 @@
       <DependentUpon>ResourceString.idl</DependentUpon>
     </ClCompile>
     <ClCompile Include="$(GeneratedFilesDir)module.g.cpp" />
+    <ClCompile Include="FontIconGlyphClassifier.cpp">
+      <DependentUpon>FontIconGlyphClassifier.idl</DependentUpon>
+    </ClCompile>
   </ItemGroup>
   <ItemGroup>
     <Midl Include="Converters.idl" />
@@ -185,6 +191,7 @@
     <Midl Include="RunHistory.idl" />
     <Midl Include="IDirectKeyListener.idl" />
     <Midl Include="ResourceString.idl" />
+    <Midl Include="FontIconGlyphClassifier.idl" />
   </ItemGroup>
   <ItemGroup>
     <None Include="packages.config" />

src/modules/cmdpal/Tests/Microsoft.CmdPal.Ext.WebSearch.UnitTests/MockSettingsInterface.cs

@@ -2,10 +2,9 @@
 // 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;
 using System.Collections.Generic;
-using Microsoft.CmdPal.Ext.WebSearch.Commands;
 using Microsoft.CmdPal.Ext.WebSearch.Helpers;
-using Microsoft.CommandPalette.Extensions.Toolkit;
 
 namespace Microsoft.CmdPal.Ext.WebSearch.UnitTests;
 
@@ -13,34 +12,22 @@ public class MockSettingsInterface : ISettingsInterface
 {
     private readonly List<HistoryItem> _historyItems;
 
+    public event EventHandler HistoryChanged;
+
     public bool GlobalIfURI { get; set; }
 
-    public uint HistoryItemCount { get; set; }
+    public int HistoryItemCount { get; set; }
 
-    public MockSettingsInterface(uint historyItemCount = 0, bool globalIfUri = true, List<HistoryItem> mockHistory = null)
+    public IReadOnlyList<HistoryItem> HistoryItems => _historyItems;
+
+    public MockSettingsInterface(int historyItemCount = 0, bool globalIfUri = true, List<HistoryItem> mockHistory = null)
     {
         _historyItems = mockHistory ?? new List<HistoryItem>();
         GlobalIfURI = globalIfUri;
         HistoryItemCount = historyItemCount;
     }
 
-    public List<ListItem> LoadHistory()
-    {
-        var listItems = new List<ListItem>();
-        foreach (var historyItem in _historyItems)
-        {
-            listItems.Add(new ListItem(new SearchWebCommand(historyItem.SearchString, this))
-            {
-                Title = historyItem.SearchString,
-                Subtitle = historyItem.Timestamp.ToString("g", System.Globalization.CultureInfo.InvariantCulture),
-            });
-        }
-
-        listItems.Reverse();
-        return listItems;
-    }
-
-    public void SaveHistory(HistoryItem historyItem)
+    public void AddHistoryItem(HistoryItem historyItem)
     {
         if (historyItem is null)
         {
@@ -54,15 +41,18 @@ public class MockSettingsInterface : ISettingsInterface
         {
             while (_historyItems.Count > HistoryItemCount)
             {
-                _historyItems.RemoveAt(0); // Remove the oldest item
+                _historyItems.RemoveAt(0);
             }
         }
+
+        HistoryChanged?.Invoke(this, EventArgs.Empty);
     }
 
     // Helper method for testing
     public void ClearHistory()
     {
         _historyItems.Clear();
+        HistoryChanged?.Invoke(this, EventArgs.Empty);
     }
 
     // Helper method for testing

src/modules/cmdpal/Tests/Microsoft.CmdPal.Ext.WebSearch.UnitTests/QueryTests.cs

@@ -45,7 +45,7 @@ public class QueryTests : CommandPaletteUnitTestBase
     }
 
     [TestMethod]
-    public async Task LoadHistoryReturnsExpectedItems()
+    public async Task HistoryReturnsExpectedItems()
     {
         // Setup
         var mockHistoryItems = new List<HistoryItem>
@@ -77,7 +77,7 @@ public class QueryTests : CommandPaletteUnitTestBase
     }
 
     [TestMethod]
-    public async Task LoadHistoryMoreThanLimitation()
+    public async Task HistoryExceedingLimitReturnsMaxItems()
     {
         // Setup
         var mockHistoryItems = new List<HistoryItem>
@@ -109,7 +109,7 @@ public class QueryTests : CommandPaletteUnitTestBase
     }
 
     [TestMethod]
-    public async Task LoadHistoryWithDisableSetting()
+    public async Task HistoryWhenSetToNoneReturnEmptyList()
     {
         // Setup
         var mockHistoryItems = new List<HistoryItem>

src/modules/cmdpal/Tests/Microsoft.CmdPal.Ext.WebSearch.UnitTests/SettingsManagerTests.cs

@@ -0,0 +1,48 @@
+// 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;
+using System.Threading.Tasks;
+
+using Microsoft.CmdPal.Ext.UnitTestBase;
+using Microsoft.CmdPal.Ext.WebSearch.Helpers;
+using Microsoft.CmdPal.Ext.WebSearch.Pages;
+using Microsoft.VisualStudio.TestTools.UnitTesting;
+
+namespace Microsoft.CmdPal.Ext.WebSearch.UnitTests;
+
+[TestClass]
+public class SettingsManagerTests : CommandPaletteUnitTestBase
+{
+    [TestMethod]
+    public async Task HistoryChangedEventIsRaisedWhenItemIsAdded()
+    {
+        // Setup
+        var settings = new MockSettingsInterface(historyItemCount: 5);
+        var page = new WebSearchListPage(settings);
+
+        var eventRaised = false;
+
+        try
+        {
+            settings.HistoryChanged += Handler;
+
+            // Act
+            settings.AddHistoryItem(new HistoryItem("test event", DateTime.UtcNow));
+            await Task.Delay(50);
+
+            // Assert
+            Assert.IsTrue(eventRaised, "Expected HistoryChanged to be raised when saving history.");
+        }
+        finally
+        {
+            settings.HistoryChanged -= Handler;
+            page.Dispose();
+        }
+
+        return;
+
+        void Handler(object s, EventArgs e) => eventRaised = true;
+    }
+}

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.Apps/AppListItem.cs

@@ -133,17 +133,13 @@ internal sealed partial class AppListItem : ListItem
 
         newCommands.Add(new Separator());
 
-        // 0x50 = P
-        // Full key chord would be Ctrl+P
-        var pinKeyChord = KeyChordHelpers.FromModifiers(true, false, false, false, 0x50, 0);
-
         if (isPinned)
         {
             newCommands.Add(
                 new CommandContextItem(
                     new UnpinAppCommand(this.AppIdentifier))
                 {
-                    RequestedShortcut = pinKeyChord,
+                    RequestedShortcut = KeyChords.TogglePin,
                 });
         }
         else
@@ -152,7 +148,7 @@ internal sealed partial class AppListItem : ListItem
                 new CommandContextItem(
                     new PinAppCommand(this.AppIdentifier))
                 {
-                    RequestedShortcut = pinKeyChord,
+                    RequestedShortcut = KeyChords.TogglePin,
                 });
         }
 

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.Apps/KeyChords.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.CmdPal.Common.Helpers;
+using Microsoft.CommandPalette.Extensions;
+
+namespace Microsoft.CmdPal.Ext.Apps;
+
+internal static class KeyChords
+{
+    internal static KeyChord OpenFileLocation { get; } = WellKnownKeyChords.OpenFileLocation;
+
+    internal static KeyChord CopyFilePath { get; } = WellKnownKeyChords.CopyFilePath;
+
+    internal static KeyChord OpenInConsole { get; } = WellKnownKeyChords.OpenInConsole;
+
+    internal static KeyChord RunAsAdministrator { get; } = WellKnownKeyChords.RunAsAdministrator;
+
+    internal static KeyChord RunAsDifferentUser { get; } = WellKnownKeyChords.RunAsDifferentUser;
+
+    internal static KeyChord TogglePin { get; } = WellKnownKeyChords.TogglePin;
+}

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.Apps/Microsoft.CmdPal.Ext.Apps.csproj

@@ -25,6 +25,7 @@
 
     <ProjectReference Include="..\..\..\..\common\ManagedCommon\ManagedCommon.csproj" />
     <ProjectReference Include="..\..\..\..\common\ManagedCsWin32\ManagedCsWin32.csproj" />
+    <ProjectReference Include="..\..\Microsoft.CmdPal.Common\Microsoft.CmdPal.Common.csproj" />
     <!-- CmdPal Toolkit reference now included via Common.ExtDependencies.props -->
   </ItemGroup>
 

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.Apps/Programs/UWPApplication.cs

@@ -87,7 +87,7 @@ public class UWPApplication : IUWPApplication
                 new CommandContextItem(
                     new RunAsAdminCommand(UniqueIdentifier, string.Empty, true))
                 {
-                    RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: VirtualKey.Enter),
+                    RequestedShortcut = KeyChords.RunAsAdministrator,
                 });
 
             // We don't add context menu to 'run as different user', because UWP applications normally installed per user and not for all users.
@@ -97,7 +97,7 @@ public class UWPApplication : IUWPApplication
             new CommandContextItem(
                 new CopyTextCommand(Location) { Name = Resources.copy_path })
             {
-                RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: VirtualKey.C),
+                RequestedShortcut = KeyChords.CopyFilePath,
             });
 
         commands.Add(
@@ -107,14 +107,14 @@ public class UWPApplication : IUWPApplication
                     Name = Resources.open_containing_folder,
                 })
             {
-                RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: VirtualKey.E),
+                RequestedShortcut = KeyChords.OpenFileLocation,
             });
 
         commands.Add(
         new CommandContextItem(
             new OpenInConsoleCommand(Package.Location))
         {
-            RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: VirtualKey.R),
+            RequestedShortcut = KeyChords.OpenInConsole,
         });
 
         commands.Add(

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.Apps/Programs/Win32Program.cs

@@ -191,32 +191,32 @@ public class Win32Program : IProgram
             commands.Add(new CommandContextItem(
                     new RunAsAdminCommand(!string.IsNullOrEmpty(LnkFilePath) ? LnkFilePath : FullPath, ParentDirectory, false))
             {
-                RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: VirtualKey.Enter),
+                RequestedShortcut = KeyChords.RunAsAdministrator,
             });
 
             commands.Add(new CommandContextItem(
                     new RunAsUserCommand(!string.IsNullOrEmpty(LnkFilePath) ? LnkFilePath : FullPath, ParentDirectory))
             {
-                RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: VirtualKey.U),
+                RequestedShortcut = KeyChords.RunAsDifferentUser,
             });
         }
 
         commands.Add(new CommandContextItem(
                     new CopyTextCommand(FullPath) { Name = Resources.copy_path })
         {
-            RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: VirtualKey.C),
+            RequestedShortcut = KeyChords.CopyFilePath,
         });
 
         commands.Add(new CommandContextItem(
                     new OpenPathCommand(ParentDirectory))
         {
-            RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: VirtualKey.E),
+            RequestedShortcut = KeyChords.OpenFileLocation,
         });
 
         commands.Add(new CommandContextItem(
                     new OpenInConsoleCommand(ParentDirectory))
         {
-            RequestedShortcut = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: VirtualKey.R),
+            RequestedShortcut = KeyChords.OpenInConsole,
         });
 
         if (AppType == ApplicationType.ShortcutApplication || AppType == ApplicationType.ApprefApplication || AppType == ApplicationType.Win32Application)

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.ClipboardHistory/ClipboardHistoryCommandsProvider.cs

@@ -2,6 +2,7 @@
 // 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.Ext.ClipboardHistory.Helpers;
 using Microsoft.CmdPal.Ext.ClipboardHistory.Pages;
 using Microsoft.CommandPalette.Extensions;
 using Microsoft.CommandPalette.Extensions.Toolkit;
@@ -11,19 +12,25 @@ namespace Microsoft.CmdPal.Ext.ClipboardHistory;
 public partial class ClipboardHistoryCommandsProvider : CommandProvider
 {
     private readonly ListItem _clipboardHistoryListItem;
+    private readonly SettingsManager _settingsManager = new();
 
     public ClipboardHistoryCommandsProvider()
     {
-        _clipboardHistoryListItem = new ListItem(new ClipboardHistoryListPage())
+        _clipboardHistoryListItem = new ListItem(new ClipboardHistoryListPage(_settingsManager))
         {
             Title = Properties.Resources.list_item_title,
             Subtitle = Properties.Resources.list_item_subtitle,
             Icon = Icons.ClipboardListIcon,
+            MoreCommands = [
+                new CommandContextItem(_settingsManager.Settings.SettingsPage),
+            ],
         };
 
         DisplayName = Properties.Resources.provider_display_name;
         Icon = Icons.ClipboardListIcon;
         Id = "Windows.ClipboardHistory";
+
+        Settings = _settingsManager.Settings;
     }
 
     public override IListItem[] TopLevelCommands()

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.ClipboardHistory/Commands/DeleteItemCommand.cs

@@ -0,0 +1,31 @@
+// 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.Ext.ClipboardHistory.Models;
+using Microsoft.CommandPalette.Extensions.Toolkit;
+using Windows.ApplicationModel.DataTransfer;
+
+namespace Microsoft.CmdPal.Ext.ClipboardHistory.Commands;
+
+internal sealed partial class DeleteItemCommand : InvokableCommand
+{
+    private readonly ClipboardItem _clipboardItem;
+
+    internal DeleteItemCommand(ClipboardItem clipboardItem)
+    {
+        _clipboardItem = clipboardItem;
+        Name = Properties.Resources.delete_command_name;
+        Icon = Icons.DeleteIcon;
+    }
+
+    public override CommandResult Invoke()
+    {
+        Clipboard.DeleteItemFromHistory(_clipboardItem.Item);
+        return CommandResult.ShowToast(new ToastArgs
+        {
+            Message = Properties.Resources.delete_toast_text,
+            Result = CommandResult.KeepOpen(),
+        });
+    }
+}

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.ClipboardHistory/Commands/PasteCommand.cs

@@ -4,6 +4,7 @@
 
 using CommunityToolkit.Mvvm.Messaging;
 using Microsoft.CmdPal.Common.Messages;
+using Microsoft.CmdPal.Ext.ClipboardHistory.Helpers;
 using Microsoft.CmdPal.Ext.ClipboardHistory.Models;
 using Microsoft.CommandPalette.Extensions.Toolkit;
 using Windows.ApplicationModel.DataTransfer;
@@ -14,11 +15,13 @@ internal sealed partial class PasteCommand : InvokableCommand
 {
     private readonly ClipboardItem _clipboardItem;
     private readonly ClipboardFormat _clipboardFormat;
+    private readonly ISettingOptions _settings;
 
-    internal PasteCommand(ClipboardItem clipboardItem, ClipboardFormat clipboardFormat)
+    internal PasteCommand(ClipboardItem clipboardItem, ClipboardFormat clipboardFormat, ISettingOptions settings)
     {
         _clipboardItem = clipboardItem;
         _clipboardFormat = clipboardFormat;
+        _settings = settings;
         Name = Properties.Resources.paste_command_name;
         Icon = Icons.PasteIcon;
     }
@@ -39,7 +42,11 @@ internal sealed partial class PasteCommand : InvokableCommand
 
         ClipboardHelper.SendPasteKeyCombination();
 
-        Clipboard.DeleteItemFromHistory(_clipboardItem.Item);
+        if (!_settings.KeepAfterPaste)
+        {
+            Clipboard.DeleteItemFromHistory(_clipboardItem.Item);
+        }
+
         return CommandResult.ShowToast(Properties.Resources.paste_toast_text);
     }
 }

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.ClipboardHistory/Helpers/ISettingOptions.cs

@@ -0,0 +1,12 @@
+// 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.Ext.ClipboardHistory.Helpers;
+
+public interface ISettingOptions
+{
+    bool KeepAfterPaste { get; }
+
+    bool DeleteFromHistoryRequiresConfirmation { get; }
+}

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.ClipboardHistory/Helpers/SettingsManager.cs

@@ -0,0 +1,54 @@
+// 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.IO;
+using Microsoft.CmdPal.Ext.ClipboardHistory.Properties;
+using Microsoft.CommandPalette.Extensions.Toolkit;
+
+namespace Microsoft.CmdPal.Ext.ClipboardHistory.Helpers;
+
+internal sealed class SettingsManager : JsonSettingsManager, ISettingOptions
+{
+    private const string Namespace = "clipboardHistory";
+
+    private static string Namespaced(string propertyName) => $"{Namespace}.{propertyName}";
+
+    private readonly ToggleSetting _keepAfterPaste = new(
+        Namespaced(nameof(KeepAfterPaste)),
+        Resources.settings_keep_after_paste_title!,
+        Resources.settings_keep_after_paste_description!,
+        false);
+
+    private readonly ToggleSetting _confirmDelete = new(
+        Namespaced(nameof(DeleteFromHistoryRequiresConfirmation)),
+        Resources.settings_confirm_delete_title!,
+        Resources.settings_confirm_delete_description!,
+        true);
+
+    public bool KeepAfterPaste => _keepAfterPaste.Value;
+
+    public bool DeleteFromHistoryRequiresConfirmation => _confirmDelete.Value;
+
+    private static string SettingsJsonPath()
+    {
+        var directory = Utilities.BaseSettingsPath("Microsoft.CmdPal");
+        Directory.CreateDirectory(directory);
+
+        // now, the state is just next to the exe
+        return Path.Combine(directory, "settings.json");
+    }
+
+    public SettingsManager()
+    {
+        FilePath = SettingsJsonPath();
+
+        Settings.Add(_keepAfterPaste);
+        Settings.Add(_confirmDelete);
+
+        // Load settings from file upon initialization
+        LoadSettings();
+
+        Settings.SettingsChanged += (_, _) => SaveSettings();
+    }
+}

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.ClipboardHistory/Icons.cs

@@ -14,5 +14,7 @@ internal sealed class Icons
 
     internal static IconInfo PasteIcon { get; } = new("\uE77F");
 
+    internal static IconInfo DeleteIcon { get; } = new("\uE74D");
+
     internal static IconInfo ClipboardListIcon { get; } = IconHelpers.FromRelativePath("Assets\\ClipboardHistory.svg");
 }

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.ClipboardHistory/KeyChords.cs

@@ -0,0 +1,19 @@
+// 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;
+using System.Collections.Generic;
+using System.Linq;
+using System.Text;
+using System.Threading.Tasks;
+using Microsoft.CommandPalette.Extensions;
+using Microsoft.CommandPalette.Extensions.Toolkit;
+using Windows.System;
+
+namespace Microsoft.CmdPal.Ext.ClipboardHistory;
+
+internal static class KeyChords
+{
+    internal static KeyChord DeleteEntry { get; } = KeyChordHelpers.FromModifiers(ctrl: true, shift: true, vkey: VirtualKey.Delete);
+}

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.ClipboardHistory/Models/ClipboardItem.cs

@@ -7,7 +7,9 @@ using System.Collections.Generic;
 using System.Diagnostics.CodeAnalysis;
 using System.Globalization;
 using System.Linq;
+using Microsoft.CmdPal.Common.Commands;
 using Microsoft.CmdPal.Ext.ClipboardHistory.Commands;
+using Microsoft.CmdPal.Ext.ClipboardHistory.Helpers;
 using Microsoft.CommandPalette.Extensions.Toolkit;
 using Windows.ApplicationModel.DataTransfer;
 using Windows.Storage.Streams;
@@ -16,9 +18,11 @@ namespace Microsoft.CmdPal.Ext.ClipboardHistory.Models;
 
 public class ClipboardItem
 {
-    public string? Content { get; set; }
+    public string? Content { get; init; }
 
-    public required ClipboardHistoryItem Item { get; set; }
+    public required ClipboardHistoryItem Item { get; init; }
+
+    public required ISettingOptions Settings { get; init; }
 
     public DateTimeOffset Timestamp => Item?.Timestamp ?? DateTimeOffset.MinValue;
 
@@ -87,6 +91,19 @@ public class ClipboardItem
             Data = new DetailsLink(Item.Timestamp.DateTime.ToString(DateTimeFormatInfo.CurrentInfo)),
         });
 
+        var deleteConfirmationCommand = new ConfirmableCommand()
+        {
+            Command = new DeleteItemCommand(this),
+            ConfirmationTitle = Properties.Resources.delete_confirmation_title!,
+            ConfirmationMessage = Properties.Resources.delete_confirmation_message!,
+            IsConfirmationRequired = () => Settings.DeleteFromHistoryRequiresConfirmation,
+        };
+        var deleteContextMenuItem = new CommandContextItem(deleteConfirmationCommand)
+        {
+            IsCritical = true,
+            RequestedShortcut = KeyChords.DeleteEntry,
+        };
+
         if (IsImage)
         {
             var iconData = new IconData(ImageData);
@@ -103,7 +120,9 @@ public class ClipboardItem
                     Metadata = metadata.ToArray(),
                 },
                 MoreCommands = [
-                    new CommandContextItem(new PasteCommand(this, ClipboardFormat.Image))
+                    new CommandContextItem(new PasteCommand(this, ClipboardFormat.Image, Settings)),
+                    new Separator(),
+                    deleteContextMenuItem,
                 ],
             };
         }
@@ -126,8 +145,10 @@ public class ClipboardItem
                     Metadata = metadata.ToArray(),
                 },
                 MoreCommands = [
-                                new CommandContextItem(new PasteCommand(this, ClipboardFormat.Text)),
-                            ],
+                    new CommandContextItem(new PasteCommand(this, ClipboardFormat.Text, Settings)),
+                    new Separator(),
+                    deleteContextMenuItem,
+                ],
             };
         }
         else

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.ClipboardHistory/Pages/ClipboardHistoryListPage.cs

@@ -7,6 +7,7 @@ using System.Collections.Generic;
 using System.Collections.ObjectModel;
 using System.Threading;
 using System.Threading.Tasks;
+using Microsoft.CmdPal.Ext.ClipboardHistory.Helpers;
 using Microsoft.CmdPal.Ext.ClipboardHistory.Models;
 using Microsoft.CommandPalette.Extensions;
 using Microsoft.CommandPalette.Extensions.Toolkit;
@@ -17,11 +18,15 @@ namespace Microsoft.CmdPal.Ext.ClipboardHistory.Pages;
 
 internal sealed partial class ClipboardHistoryListPage : ListPage
 {
+    private readonly SettingsManager _settingsManager;
     private readonly ObservableCollection<ClipboardItem> clipboardHistory;
     private readonly string _defaultIconPath;
 
-    public ClipboardHistoryListPage()
+    public ClipboardHistoryListPage(SettingsManager settingsManager)
     {
+        ArgumentNullException.ThrowIfNull(settingsManager);
+
+        _settingsManager = settingsManager;
         clipboardHistory = [];
         _defaultIconPath = string.Empty;
         Icon = Icons.ClipboardListIcon;
@@ -84,11 +89,11 @@ internal sealed partial class ClipboardHistoryListPage : ListPage
                 if (item.Content.Contains(StandardDataFormats.Text))
                 {
                     var text = await item.Content.GetTextAsync();
-                    items.Add(new ClipboardItem { Content = text, Item = item });
+                    items.Add(new ClipboardItem { Settings = _settingsManager, Content = text, Item = item });
                 }
                 else if (item.Content.Contains(StandardDataFormats.Bitmap))
                 {
-                    items.Add(new ClipboardItem { Item = item });
+                    items.Add(new ClipboardItem { Settings = _settingsManager, Item = item });
                 }
             }
 

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.ClipboardHistory/Properties/Resources.Designer.cs

@@ -96,6 +96,42 @@ namespace Microsoft.CmdPal.Ext.ClipboardHistory.Properties {
             }
         }
         
+        /// <summary>
+        ///   Looks up a localized string similar to Delete.
+        /// </summary>
+        public static string delete_command_name {
+            get {
+                return ResourceManager.GetString("delete_command_name", resourceCulture);
+            }
+        }
+        
+        /// <summary>
+        ///   Looks up a localized string similar to Are you sure you want to delete this item from clipboard history? This action cannot be undone..
+        /// </summary>
+        public static string delete_confirmation_message {
+            get {
+                return ResourceManager.GetString("delete_confirmation_message", resourceCulture);
+            }
+        }
+        
+        /// <summary>
+        ///   Looks up a localized string similar to Delete item?.
+        /// </summary>
+        public static string delete_confirmation_title {
+            get {
+                return ResourceManager.GetString("delete_confirmation_title", resourceCulture);
+            }
+        }
+        
+        /// <summary>
+        ///   Looks up a localized string similar to Deleted from clipboard history.
+        /// </summary>
+        public static string delete_toast_text {
+            get {
+                return ResourceManager.GetString("delete_toast_text", resourceCulture);
+            }
+        }
+        
         /// <summary>
         ///   Looks up a localized string similar to Copy, paste, and search items on the clipboard.
         /// </summary>
@@ -140,5 +176,41 @@ namespace Microsoft.CmdPal.Ext.ClipboardHistory.Properties {
                 return ResourceManager.GetString("provider_display_name", resourceCulture);
             }
         }
+        
+        /// <summary>
+        ///   Looks up a localized string similar to .
+        /// </summary>
+        public static string settings_confirm_delete_description {
+            get {
+                return ResourceManager.GetString("settings_confirm_delete_description", resourceCulture);
+            }
+        }
+        
+        /// <summary>
+        ///   Looks up a localized string similar to Show a confirmation dialog when manually deleting an item.
+        /// </summary>
+        public static string settings_confirm_delete_title {
+            get {
+                return ResourceManager.GetString("settings_confirm_delete_title", resourceCulture);
+            }
+        }
+        
+        /// <summary>
+        ///   Looks up a localized string similar to .
+        /// </summary>
+        public static string settings_keep_after_paste_description {
+            get {
+                return ResourceManager.GetString("settings_keep_after_paste_description", resourceCulture);
+            }
+        }
+        
+        /// <summary>
+        ///   Looks up a localized string similar to Keep items in clipboard history after pasting.
+        /// </summary>
+        public static string settings_keep_after_paste_title {
+            get {
+                return ResourceManager.GetString("settings_keep_after_paste_title", resourceCulture);
+            }
+        }
     }
 }

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.ClipboardHistory/Properties/Resources.resx

@@ -144,4 +144,28 @@
   <data name="clipboard_failed_to_load" xml:space="preserve">
     <value>Loading clipboard history failed</value>
   </data>
+  <data name="delete_command_name" xml:space="preserve">
+    <value>Delete</value>
+  </data>
+  <data name="delete_toast_text" xml:space="preserve">
+    <value>Deleted from clipboard history</value>
+  </data>
+  <data name="settings_keep_after_paste_description" xml:space="preserve">
+    <value />
+  </data>
+  <data name="settings_keep_after_paste_title" xml:space="preserve">
+    <value>Keep items in clipboard history after pasting</value>
+  </data>
+  <data name="settings_confirm_delete_title" xml:space="preserve">
+    <value>Show a confirmation dialog when manually deleting an item</value>
+  </data>
+  <data name="settings_confirm_delete_description" xml:space="preserve">
+    <value />
+  </data>
+  <data name="delete_confirmation_title" xml:space="preserve">
+    <value>Delete item?</value>
+  </data>
+  <data name="delete_confirmation_message" xml:space="preserve">
+    <value>Are you sure you want to delete this item from clipboard history? This action cannot be undone.</value>
+  </data>
 </root>

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.Indexer/Data/IndexerListItem.cs

@@ -91,9 +91,9 @@ internal sealed partial class IndexerListItem : ListItem
         }
 
         commands.Add(new CommandContextItem(new OpenWithCommand(fullPath)));
-        commands.Add(new CommandContextItem(new ShowFileInFolderCommand(fullPath) { Name = Resources.Indexer_Command_ShowInFolder }));
-        commands.Add(new CommandContextItem(new CopyPathCommand(fullPath) { Name = Resources.Indexer_Command_CopyPath }));
-        commands.Add(new CommandContextItem(new OpenInConsoleCommand(fullPath)));
+        commands.Add(new CommandContextItem(new ShowFileInFolderCommand(fullPath) { Name = Resources.Indexer_Command_ShowInFolder }) { RequestedShortcut = KeyChords.OpenFileLocation });
+        commands.Add(new CommandContextItem(new CopyPathCommand(fullPath) { Name = Resources.Indexer_Command_CopyPath }) { RequestedShortcut = KeyChords.CopyFilePath });
+        commands.Add(new CommandContextItem(new OpenInConsoleCommand(fullPath)) { RequestedShortcut = KeyChords.OpenInConsole });
         commands.Add(new CommandContextItem(new OpenPropertiesCommand(fullPath)));
 
         if (IsActionsFeatureEnabled && ApiInformation.IsApiContractPresent("Windows.AI.Actions.ActionsContract", 4))

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.Indexer/KeyChords.cs

@@ -0,0 +1,17 @@
+// 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.Common.Helpers;
+using Microsoft.CommandPalette.Extensions;
+
+namespace Microsoft.CmdPal.Ext.Indexer;
+
+internal static class KeyChords
+{
+    internal static KeyChord OpenFileLocation { get; } = WellKnownKeyChords.OpenFileLocation;
+
+    internal static KeyChord CopyFilePath { get; } = WellKnownKeyChords.CopyFilePath;
+
+    internal static KeyChord OpenInConsole { get; } = WellKnownKeyChords.OpenInConsole;
+}

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.WebSearch/Commands/SearchWebCommand.cs

@@ -36,7 +36,7 @@ internal sealed partial class SearchWebCommand : InvokableCommand
 
         if (_settingsManager.HistoryItemCount != 0)
         {
-            _settingsManager.SaveHistory(new HistoryItem(Arguments, DateTime.Now));
+            _settingsManager.AddHistoryItem(new HistoryItem(Arguments, DateTime.Now));
         }
 
         return CommandResult.Dismiss();

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.WebSearch/Helpers/HistoryStore.cs

@@ -0,0 +1,119 @@
+// 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;
+using System.Collections.Generic;
+using System.IO;
+using System.Text.Json;
+using System.Threading;
+using ManagedCommon;
+
+namespace Microsoft.CmdPal.Ext.WebSearch.Helpers;
+
+internal sealed class HistoryStore
+{
+    private readonly string _filePath;
+    private readonly List<HistoryItem> _items = [];
+    private readonly Lock _lock = new();
+
+    private int _capacity;
+
+    public event EventHandler? Changed;
+
+    public HistoryStore(string filePath, int capacity)
+    {
+        ArgumentNullException.ThrowIfNull(filePath);
+        ArgumentOutOfRangeException.ThrowIfNegative(capacity);
+
+        _filePath = filePath;
+        _capacity = capacity;
+
+        _items.AddRange(LoadFromDiskSafe());
+        TrimNoLock();
+    }
+
+    public IReadOnlyList<HistoryItem> HistoryItems
+    {
+        get
+        {
+            lock (_lock)
+            {
+                return [.. _items];
+            }
+        }
+    }
+
+    public void Add(HistoryItem item)
+    {
+        ArgumentNullException.ThrowIfNull(item);
+
+        lock (_lock)
+        {
+            _items.Add(item);
+            _ = TrimNoLock();
+            SaveNoLock();
+        }
+
+        Changed?.Invoke(this, EventArgs.Empty);
+    }
+
+    public void SetCapacity(int capacity)
+    {
+        ArgumentOutOfRangeException.ThrowIfNegative(capacity);
+
+        bool trimmed;
+        lock (_lock)
+        {
+            _capacity = capacity;
+            trimmed = TrimNoLock();
+            if (trimmed)
+            {
+                SaveNoLock();
+            }
+        }
+
+        if (trimmed)
+        {
+            Changed?.Invoke(this, EventArgs.Empty);
+        }
+    }
+
+    private bool TrimNoLock()
+    {
+        var max = _capacity;
+        if (_items.Count > max)
+        {
+            _items.RemoveRange(0, _items.Count - max);
+            return true;
+        }
+
+        return false;
+    }
+
+    private List<HistoryItem> LoadFromDiskSafe()
+    {
+        try
+        {
+            if (!File.Exists(_filePath))
+            {
+                return [];
+            }
+
+            var fileContent = File.ReadAllText(_filePath);
+            var historyItems = JsonSerializer.Deserialize<List<HistoryItem>>(fileContent, WebSearchJsonSerializationContext.Default.ListHistoryItem) ?? [];
+            return historyItems;
+        }
+        catch (Exception ex)
+        {
+            Logger.LogError("Unable to load history", ex);
+            return [];
+        }
+    }
+
+    private void SaveNoLock()
+    {
+        var json = JsonSerializer.Serialize(_items, WebSearchJsonSerializationContext.Default.ListHistoryItem);
+        File.WriteAllText(_filePath, json);
+    }
+}

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.WebSearch/Helpers/ISettingsInterface.cs

@@ -2,6 +2,7 @@
 // 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;
 using System.Collections.Generic;
 using Microsoft.CommandPalette.Extensions.Toolkit;
 
@@ -9,11 +10,13 @@ namespace Microsoft.CmdPal.Ext.WebSearch.Helpers;
 
 public interface ISettingsInterface
 {
+    event EventHandler? HistoryChanged;
+
     public bool GlobalIfURI { get; }
 
-    public uint HistoryItemCount { get; }
+    public int HistoryItemCount { get; }
 
-    public List<ListItem> LoadHistory();
+    public IReadOnlyList<HistoryItem> HistoryItems { get; }
 
-    public void SaveHistory(HistoryItem historyItem);
+    public void AddHistoryItem(HistoryItem historyItem);
 }

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.WebSearch/Helpers/SettingsManager.cs

@@ -4,11 +4,8 @@
 
 using System;
 using System.Collections.Generic;
-using System.Globalization;
 using System.IO;
-using System.Linq;
-using System.Text.Json;
-using Microsoft.CmdPal.Ext.WebSearch.Commands;
+using ManagedCommon;
 using Microsoft.CmdPal.Ext.WebSearch.Properties;
 using Microsoft.CommandPalette.Extensions.Toolkit;
 
@@ -17,10 +14,16 @@ namespace Microsoft.CmdPal.Ext.WebSearch.Helpers;
 public class SettingsManager : JsonSettingsManager, ISettingsInterface
 {
     private const string HistoryItemCountLegacySettingsKey = "ShowHistory";
-    private readonly string _historyPath;
-
     private static readonly string _namespace = "websearch";
 
+    public event EventHandler? HistoryChanged
+    {
+        add => _history.Changed += value;
+        remove => _history.Changed -= value;
+    }
+
+    private readonly HistoryStore _history;
+
     private static string Namespaced(string propertyName) => $"{_namespace}.{propertyName}";
 
     private static readonly List<ChoiceSetSetting.Choice> _choices =
@@ -46,9 +49,26 @@ public class SettingsManager : JsonSettingsManager, ISettingsInterface
 
     public bool GlobalIfURI => _globalIfURI.Value;
 
-    public uint HistoryItemCount => uint.TryParse(_historyItemCount.Value, out var value) ? value : 0;
+    public int HistoryItemCount => int.TryParse(_historyItemCount.Value, out var value) && value >= 0 ? value : 0;
 
-    internal static string SettingsJsonPath()
+    public IReadOnlyList<HistoryItem> HistoryItems => _history.HistoryItems;
+
+    public SettingsManager()
+    {
+        FilePath = SettingsJsonPath();
+
+        Settings.Add(_globalIfURI);
+        Settings.Add(_historyItemCount);
+
+        LoadSettings();
+
+        // Initialize history store after loading settings to get the correct capacity
+        _history = new HistoryStore(HistoryStateJsonPath(), HistoryItemCount);
+
+        Settings.SettingsChanged += (_, _) => SaveSettings();
+    }
+
+    private static string SettingsJsonPath()
     {
         var directory = Utilities.BaseSettingsPath("Microsoft.CmdPal");
         Directory.CreateDirectory(directory);
@@ -57,7 +77,7 @@ public class SettingsManager : JsonSettingsManager, ISettingsInterface
         return Path.Combine(directory, "settings.json");
     }
 
-    internal static string HistoryStateJsonPath()
+    private static string HistoryStateJsonPath()
     {
         var directory = Utilities.BaseSettingsPath("Microsoft.CmdPal");
         Directory.CreateDirectory(directory);
@@ -66,156 +86,30 @@ public class SettingsManager : JsonSettingsManager, ISettingsInterface
         return Path.Combine(directory, "websearch_history.json");
     }
 
-    public void SaveHistory(HistoryItem historyItem)
+    public void AddHistoryItem(HistoryItem historyItem)
     {
-        if (historyItem is null)
-        {
-            return;
-        }
-
         try
         {
-            List<HistoryItem> historyItems;
-
-            // Check if the file exists and load existing history
-            if (File.Exists(_historyPath))
-            {
-                var existingContent = File.ReadAllText(_historyPath);
-                historyItems = JsonSerializer.Deserialize<List<HistoryItem>>(existingContent, WebSearchJsonSerializationContext.Default.ListHistoryItem) ?? [];
-            }
-            else
-            {
-                historyItems = [];
-            }
-
-            // Add the new history item
-            historyItems.Add(historyItem);
-
-            // Determine the maximum number of items to keep based on HistoryItemCount
-            if (HistoryItemCount > 0)
-            {
-                // Keep only the most recent `maxHistoryItems` items
-                while (historyItems.Count > HistoryItemCount)
-                {
-                    historyItems.RemoveAt(0); // Remove the oldest item
-                }
-            }
-
-            // Serialize the updated list back to JSON and save it
-            var historyJson = JsonSerializer.Serialize(historyItems, WebSearchJsonSerializationContext.Default.ListHistoryItem);
-            File.WriteAllText(_historyPath, historyJson);
+            _history.Add(historyItem);
         }
         catch (Exception ex)
         {
+            Logger.LogError("Failed to add item to the search history", ex);
             ExtensionHost.LogMessage(new LogMessage() { Message = ex.ToString() });
         }
     }
 
-    public List<ListItem> LoadHistory()
-    {
-        try
-        {
-            if (!File.Exists(_historyPath))
-            {
-                return [];
-            }
-
-            // Read and deserialize JSON into a list of HistoryItem objects
-            var fileContent = File.ReadAllText(_historyPath);
-            var historyItems = JsonSerializer.Deserialize<List<HistoryItem>>(fileContent, WebSearchJsonSerializationContext.Default.ListHistoryItem) ?? [];
-
-            // Convert each HistoryItem to a ListItem
-            var listItems = new List<ListItem>();
-            foreach (var historyItem in historyItems)
-            {
-                listItems.Add(new ListItem(new SearchWebCommand(historyItem.SearchString, this))
-                {
-                    Title = historyItem.SearchString,
-                    Subtitle = historyItem.Timestamp.ToString("g", CultureInfo.InvariantCulture), // Ensures consistent formatting
-                });
-            }
-
-            listItems.Reverse();
-            return listItems;
-        }
-        catch (Exception ex)
-        {
-            ExtensionHost.LogMessage(new LogMessage() { Message = ex.ToString() });
-            return [];
-        }
-    }
-
-    public SettingsManager()
-    {
-        FilePath = SettingsJsonPath();
-        _historyPath = HistoryStateJsonPath();
-
-        Settings.Add(_globalIfURI);
-        Settings.Add(_historyItemCount);
-
-        // Load settings from file upon initialization
-        LoadSettings();
-
-        Settings.SettingsChanged += (s, a) => this.SaveSettings();
-    }
-
-    private void ClearHistory()
-    {
-        try
-        {
-            if (File.Exists(_historyPath))
-            {
-                // Delete the history file
-                File.Delete(_historyPath);
-
-                // Log that the history was successfully cleared
-                ExtensionHost.LogMessage(new LogMessage() { Message = "History cleared successfully." });
-            }
-            else
-            {
-                // Log that there was no history file to delete
-                ExtensionHost.LogMessage(new LogMessage() { Message = "No history file found to clear." });
-            }
-        }
-        catch (Exception ex)
-        {
-            // Log any exception that occurs
-            ExtensionHost.LogMessage(new LogMessage() { Message = $"Failed to clear history: {ex}" });
-        }
-    }
-
     public override void SaveSettings()
     {
         base.SaveSettings();
+
         try
         {
-            if (HistoryItemCount == 0)
-            {
-                ClearHistory();
-            }
-            else if (HistoryItemCount > 0)
-            {
-                // Trim the history file if there are more items than the new limit
-                if (File.Exists(_historyPath))
-                {
-                    var existingContent = File.ReadAllText(_historyPath);
-                    var historyItems = JsonSerializer.Deserialize<List<HistoryItem>>(existingContent, WebSearchJsonSerializationContext.Default.ListHistoryItem) ?? [];
-
-                    // Check if trimming is needed
-                    if (historyItems.Count > HistoryItemCount)
-                    {
-                        // Trim the list to keep only the most recent `HistoryItemCount` items
-                        historyItems = historyItems.Skip((int)(historyItems.Count - HistoryItemCount)).ToList();
-
-                        // Save the trimmed history back to the file
-                        var trimmedHistoryJson = JsonSerializer.Serialize(historyItems, WebSearchJsonSerializationContext.Default.ListHistoryItem);
-                        File.WriteAllText(_historyPath, trimmedHistoryJson);
-                    }
-                }
-            }
+            _history.SetCapacity(HistoryItemCount);
         }
         catch (Exception ex)
         {
+            Logger.LogError("Failed to save the search history", ex);
             ExtensionHost.LogMessage(new LogMessage() { Message = ex.ToString() });
         }
     }

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.WebSearch/Pages/WebSearchListPage.cs

@@ -5,8 +5,8 @@
 using System;
 using System.Collections.Generic;
 using System.Globalization;
-using System.Linq;
 using System.Text;
+using System.Threading;
 using Microsoft.CmdPal.Ext.WebSearch.Commands;
 using Microsoft.CmdPal.Ext.WebSearch.Helpers;
 using Microsoft.CmdPal.Ext.WebSearch.Properties;
@@ -16,31 +16,30 @@ using BrowserInfo = Microsoft.CmdPal.Ext.WebSearch.Helpers.DefaultBrowserInfo;
 
 namespace Microsoft.CmdPal.Ext.WebSearch.Pages;
 
-internal sealed partial class WebSearchListPage : DynamicListPage
+internal sealed partial class WebSearchListPage : DynamicListPage, IDisposable
 {
-    private readonly string _iconPath = string.Empty;
-    private readonly List<ListItem>? _historyItems;
+    private readonly IconInfo _newSearchIcon = new(string.Empty);
     private readonly ISettingsInterface _settingsManager;
+    private readonly Lock _sync = new();
     private static readonly CompositeFormat PluginInBrowserName = System.Text.CompositeFormat.Parse(Properties.Resources.plugin_in_browser_name);
     private static readonly CompositeFormat PluginOpen = System.Text.CompositeFormat.Parse(Properties.Resources.plugin_open);
-    private List<ListItem> _allItems;
+    private IListItem[] _allItems = [];
+    private List<ListItem> _historyItems = [];
 
     public WebSearchListPage(ISettingsInterface settingsManager)
     {
+        ArgumentNullException.ThrowIfNull(settingsManager);
+
         Name = Resources.command_item_title;
         Title = Resources.command_item_title;
         Icon = IconHelpers.FromRelativePath("Assets\\WebSearch.png");
-        _allItems = [];
         Id = "com.microsoft.cmdpal.websearch";
+
         _settingsManager = settingsManager;
-        _historyItems = _settingsManager.HistoryItemCount != 0 ? _settingsManager.LoadHistory() : null;
-        if (_historyItems is not null)
-        {
-            _allItems.AddRange(_historyItems);
-        }
+        _settingsManager.HistoryChanged += SettingsManagerOnHistoryChanged;
 
         // It just looks viewer to have string twice on the page, and default placeholder is good enough
-        PlaceholderText = _allItems.Count > 0 ? Resources.plugin_description : string.Empty;
+        PlaceholderText = _allItems.Length > 0 ? Resources.plugin_description : string.Empty;
 
         EmptyContent = new CommandItem(new NoOpCommand())
         {
@@ -48,45 +47,102 @@ internal sealed partial class WebSearchListPage : DynamicListPage
             Title = Properties.Resources.plugin_description,
             Subtitle = string.Format(CultureInfo.CurrentCulture, PluginInBrowserName, BrowserInfo.Name ?? BrowserInfo.MSEdgeName),
         };
+
+        UpdateHistory();
+        RequeryAndUpdateItems(SearchText);
     }
 
-    public List<ListItem> Query(string query)
+    private void SettingsManagerOnHistoryChanged(object? sender, EventArgs e)
     {
-        ArgumentNullException.ThrowIfNull(query);
-        IEnumerable<ListItem>? filteredHistoryItems = null;
+        UpdateHistory();
+        RequeryAndUpdateItems(SearchText);
+    }
 
-        if (_historyItems is not null)
+    private void UpdateHistory()
+    {
+        List<ListItem> history = [];
+
+        if (_settingsManager.HistoryItemCount > 0)
         {
-            filteredHistoryItems = _settingsManager.HistoryItemCount != 0 ? ListHelpers.FilterList(_historyItems, query).OfType<ListItem>() : null;
+            var items = _settingsManager.HistoryItems;
+            for (var index = items.Count - 1; index >= 0; index--)
+            {
+                var historyItem = items[index];
+                history.Add(new ListItem(new SearchWebCommand(historyItem.SearchString, _settingsManager))
+                {
+                    Title = historyItem.SearchString,
+                    Subtitle = historyItem.Timestamp.ToString("g", CultureInfo.InvariantCulture),
+                });
+            }
         }
 
-        var results = new List<ListItem>();
+        lock (_sync)
+        {
+            _historyItems = history;
+        }
+    }
+
+    private static IListItem[] Query(string query, List<ListItem> historySnapshot, ISettingsInterface settingsManager, IconInfo newSearchIcon)
+    {
+        ArgumentNullException.ThrowIfNull(query);
+
+        var filteredHistoryItems = settingsManager.HistoryItemCount > 0
+            ? ListHelpers.FilterList(historySnapshot, query)
+            : [];
+
+        var results = new List<IListItem>();
 
         if (!string.IsNullOrEmpty(query))
         {
             var searchTerm = query;
-            var result = new ListItem(new SearchWebCommand(searchTerm, _settingsManager))
+            var result = new ListItem(new SearchWebCommand(searchTerm, settingsManager))
             {
                 Title = searchTerm,
                 Subtitle = string.Format(CultureInfo.CurrentCulture, PluginOpen, BrowserInfo.Name ?? BrowserInfo.MSEdgeName),
-                Icon = new IconInfo(_iconPath),
+                Icon = newSearchIcon,
             };
             results.Add(result);
         }
 
-        if (filteredHistoryItems is not null)
+        results.AddRange(filteredHistoryItems);
+
+        return [.. results];
+    }
+
+    private void RequeryAndUpdateItems(string search)
+    {
+        List<ListItem> historySnapshot;
+        lock (_sync)
         {
-            results.AddRange(filteredHistoryItems);
+            historySnapshot = _historyItems;
         }
 
-        return results;
+        var items = Query(search ?? string.Empty, historySnapshot, _settingsManager, _newSearchIcon);
+
+        lock (_sync)
+        {
+            _allItems = items;
+        }
+
+        RaiseItemsChanged();
     }
 
     public override void UpdateSearchText(string oldSearch, string newSearch)
     {
-        _allItems = [.. Query(newSearch)];
-        RaiseItemsChanged(0);
+        RequeryAndUpdateItems(newSearch);
     }
 
-    public override IListItem[] GetItems() => [.. _allItems];
+    public override IListItem[] GetItems()
+    {
+        lock (_sync)
+        {
+            return _allItems;
+        }
+    }
+
+    public void Dispose()
+    {
+        _settingsManager.HistoryChanged -= SettingsManagerOnHistoryChanged;
+        GC.SuppressFinalize(this);
+    }
 }

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.WebSearch/WebSearchCommandsProvider.cs

@@ -2,6 +2,7 @@
 // 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;
 using Microsoft.CmdPal.Ext.WebSearch.Commands;
 using Microsoft.CmdPal.Ext.WebSearch.Helpers;
 using Microsoft.CmdPal.Ext.WebSearch.Properties;
@@ -15,6 +16,9 @@ public partial class WebSearchCommandsProvider : CommandProvider
     private readonly SettingsManager _settingsManager = new();
     private readonly FallbackExecuteSearchItem _fallbackItem;
     private readonly FallbackOpenURLItem _openUrlFallbackItem;
+    private readonly WebSearchTopLevelCommandItem _webSearchTopLevelItem;
+    private readonly ICommandItem[] _topLevelItems;
+    private readonly IFallbackCommandItem[] _fallbackCommands;
 
     public WebSearchCommandsProvider()
     {
@@ -25,18 +29,27 @@ public partial class WebSearchCommandsProvider : CommandProvider
 
         _fallbackItem = new FallbackExecuteSearchItem(_settingsManager);
         _openUrlFallbackItem = new FallbackOpenURLItem(_settingsManager);
-    }
 
-    public override ICommandItem[] TopLevelCommands()
-    {
-        return [new WebSearchTopLevelCommandItem(_settingsManager)
+        _webSearchTopLevelItem = new WebSearchTopLevelCommandItem(_settingsManager)
         {
-            MoreCommands = [
+            MoreCommands =
+            [
                 new CommandContextItem(Settings!.SettingsPage),
             ],
-        }
-        ];
+        };
+        _topLevelItems = [_webSearchTopLevelItem];
+        _fallbackCommands = [_openUrlFallbackItem, _fallbackItem];
     }
 
-    public override IFallbackCommandItem[]? FallbackCommands() => [_openUrlFallbackItem, _fallbackItem];
+    public override ICommandItem[] TopLevelCommands() => _topLevelItems;
+
+    public override IFallbackCommandItem[]? FallbackCommands() => _fallbackCommands;
+
+    public override void Dispose()
+    {
+        _webSearchTopLevelItem?.Dispose();
+
+        base.Dispose();
+        GC.SuppressFinalize(this);
+    }
 }

src/modules/cmdpal/ext/Microsoft.CmdPal.Ext.WebSearch/WebSearchTopLevelCommandItem.cs

@@ -3,7 +3,6 @@
 // See the LICENSE file in the project root for more information.
 
 using System;
-using System.IO;
 using Microsoft.CmdPal.Ext.WebSearch.Commands;
 using Microsoft.CmdPal.Ext.WebSearch.Helpers;
 using Microsoft.CmdPal.Ext.WebSearch.Pages;
@@ -13,7 +12,7 @@ using Microsoft.CommandPalette.Extensions.Toolkit;
 
 namespace Microsoft.CmdPal.Ext.WebSearch;
 
-public partial class WebSearchTopLevelCommandItem : CommandItem, IFallbackHandler
+public partial class WebSearchTopLevelCommandItem : CommandItem, IFallbackHandler, IDisposable
 {
     private readonly SettingsManager _settingsManager;
 
@@ -27,17 +26,29 @@ public partial class WebSearchTopLevelCommandItem : CommandItem, IFallbackHandle
 
     private void SetDefaultTitle() => Title = Resources.command_item_title;
 
+    private void ReplaceCommand(ICommand newCommand)
+    {
+        (Command as IDisposable)?.Dispose();
+        Command = newCommand;
+    }
+
     public void UpdateQuery(string query)
     {
         if (string.IsNullOrEmpty(query))
         {
             SetDefaultTitle();
-            Command = new WebSearchListPage(_settingsManager);
+            ReplaceCommand(new WebSearchListPage(_settingsManager));
         }
         else
         {
             Title = query;
-            Command = new SearchWebCommand(query, _settingsManager);
+            ReplaceCommand(new SearchWebCommand(query, _settingsManager));
         }
     }
+
+    public void Dispose()
+    {
+        (Command as IDisposable)?.Dispose();
+        GC.SuppressFinalize(this);
+    }
 }

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

@@ -0,0 +1,189 @@
+// 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.Linq;
+using Microsoft.CommandPalette.Extensions;
+using Microsoft.CommandPalette.Extensions.Toolkit;
+
+namespace SamplePagesExtension.Pages;
+
+internal sealed partial class SampleIconPage : ListPage
+{
+    private readonly IListItem[] _items =
+    [
+        /*
+         * Quick intro to Unicode in source code:
+         * - Every character has a code point (e.g., U+0041 = 'A').
+         * - Code points up to U+FFFF use \u1234 (4 hex digits and lowercase u).
+         * - Code points above that (up to U+10FFFF) use \U12345678 (8 hex digits and capital letter U).
+         * - If your source file is UTF-8, you can type the character directly, but it may not display properly in editors,
+         *   and it's harder to see the actual code point.
+         * - Some symbols (like many emojis) are built from multiple code points
+         *   joined together (e.g., 👋🏻 = U+1F44B + U+1F3FB).
+         *
+         * Examples:
+         *   😍 = "😍" or "\U0001F60D"
+         *   👋🏻 = "👋🏻" or "\U0001F44B\U0001F3FB"
+         *   🧙‍♂️ = "🧙‍♂️" or "\U0001F9D9\u200D\u2642\U0000FE0F"   (male mage)
+         *   🧙🏿‍♀️ = "🧙🏿‍♀️" or "\U0001F9D9\U0001F3FF\u200D\u2640\U0000FE0F" (dark-skinned woman mage)
+         *
+         */
+
+        // Emoji Smiling Face with Heart-Eyes
+        // Unicode: \U0001F60D
+        BuildIconItem("😍", "Standard emoji icon", "Basic emoji character rendered as an icon"),
+
+        // Emoji Smiling Face with Heart-Eyes
+        // Unicode: \U0001F60D\U0001F643\U0001F622
+        BuildIconItem("😍🙃😢", "Multiple emojis", "Use of multiple emojis for icon is not allowed"),
+
+        // Emoji Smiling Face with Sunglasses
+        // Unicode: \U0001F60E
+        BuildIconItem("\U0001F60E", "Unicode escape sequence emoji", "Emoji defined using Unicode escape sequence notation"),
+
+        // Segoe Fluent Icons font icon
+        // Unicode: \uE8D4
+        BuildIconItem("\uE8D4", "Segoe Fluent icon demonstration", "Segoe Fluent/MDL2 icon from system font\nWorks as an icon but won't display properly in button text"),
+
+        // Extended pictographic symbol for keyboard
+        BuildIconItem("\u2328", "Extended pictographic symbol", "Pictographic symbol representing a keyboard"),
+
+        // Capital letter A
+        BuildIconItem("A", "Simple text character as icon", "Basic letter character used as an icon demonstration"),
+
+        // Letter 1
+        // Unicode: \U00000031
+        BuildIconItem("1", "Simple text character as icon", "Basic letter character used as an icon demonstration"),
+
+        // Emoji Keycap Digit Two ... 2️⃣
+        // Unicode: \U00000032\U000020E3
+        // This is a sequence of three code points: the digit '2' (U+0032), and a combining enclosing keycap (U+20E3). No variation selector is used here.
+        BuildIconItem("\U00000032\U000020E3", "Emoji without variation selector", "Emoji character doesn't have VS16 variation selector to render as text"),
+
+        // Emoji Keycap Digit Three ... 3️⃣
+        // Unicode: \U00000033\U0000FE0F\U000020E3
+        // This is a sequence of three code points: the digit '3' (U+0033), a variation selector (U+FE0F) to specify emoji presentation, and a combining enclosing keycap (U+20E3).
+        BuildIconItem("3️⃣", "Emoji with variation selector", "Emoji character using a variation selector to specify emoji presentation"),
+
+        // Symbol #
+        // Unicode: \u0023
+        BuildIconItem("#", "Simple text character as icon", "Basic letter character used as an icon demonstration"),
+
+        // Symbol # keycap
+        // Unicode: \u0023\ufe0f\u20e3
+        // Sequence of 3 code points: symbol #, a variation selector (U+FE0F) to specify emoji presentation, and a combining enclosing keycap (U+20E3).
+        BuildIconItem("\u0023\ufe0f\u20e3", "Simple text character as icon", "Basic letter character used as an icon demonstration"),
+
+        // Capital letter WM
+        // This is two characters, which is not a valid icon representation. It will be replaced by a placeholder signalizing an invalid icon.
+        BuildIconItem("WM", "Invalid icon representation", "String with multiple characters that does not correspond to a valid single icon"),
+
+        // Emoji Mage
+        // Unicode: \U0001F9D9
+        BuildIconItem("🧙", "Single code-point emoji example", "Simple emoji character using a single Unicode code point"),
+
+        // Emoji Male Mage (Mage with gender modifier)
+        // Unicode: \U0001F9D9\u200D\u2642\uFE0F
+        BuildIconItem("🧙‍♂️", "Complex emoji with gender modifier", "Composite emoji using Zero-Width Joiner (ZWJ) sequence for male variant"),
+
+        // Emoji Woman Mage (Mage with gender modifier)
+        // Unicode: \U0001F9D9\u200D\u2640\uFE0F
+        BuildIconItem("\U0001F9D9\u200D\u2640\uFE0F", "Complex emoji with gender modifier", "Composite emoji using Zero-Width Joiner (ZWJ) sequence for female variant"),
+
+        // Emoji Waving Hand
+        // Unicode: \U0001F44B
+        BuildIconItem("👋", "Basic hand gesture emoji", "Standard emoji character representing a waving hand"),
+
+        // Emoji Waving Hand + Light Skin Tone
+        // Unicode: \U0001F44B\U0001F3FB
+        BuildIconItem("👋🏻", "Emoji with light skin tone modifier", "Emoji enhanced with Unicode skin tone modifier (light)"),
+
+        // Emoji Waving Hand + Dark Skin Tone
+        // Unicode: \U0001F44B\U0001F3FF
+        BuildIconItem("\U0001F44B\U0001F3FF", "Emoji with dark skin tone modifier", "Emoji enhanced with Unicode skin tone modifier (dark)"),
+
+        // Flag of Czechia (Czech Republic)
+        // Unicode: \U0001F1E8\U0001F1FF
+        BuildIconItem("\U0001F1E8\U0001F1FF", "Flag emoji using regional indicators", "Emoji flag constructed from regional indicator symbols for Czechia"),
+
+        // Use of ZWJ without emojis
+        // KA (\u0995) + VIRAMA (\u09CD) + ZWJ (\u200D) - shows the half-form KA
+        // Unicode: \u0995\u09CD\u200D
+        BuildIconItem("\u0995\u09CD\u200D", "Use of ZWJ in non-emoji context", "Shows the half-form KA"),
+
+        // Use of ZWJ without emojis
+        // KA (\u0995) + VIRAMA (\u09CD) + Shows full KA with an explicit virama mark (not half-form).
+        // Unicode: \u0995\u09CD
+        BuildIconItem("\u0995\u09CD", "Use of ZWJ in non-emoji context", "Shows full KA with an explicit virama mark"),
+
+        // mahjong tile red dragon (using Unicode escape sequence)
+        // https://en.wikipedia.org/wiki/Mahjong_Tiles_(Unicode_block)
+        // Unicode: \U0001F004
+        BuildIconItem("\U0001F004", "Mahjong tile emoji (red dragon)", "Mahjong tile red dragon emoji character using Unicode escape sequence"),
+
+        // mahjong tile green dragon (non-emoji)
+        // https://en.wikipedia.org/wiki/Mahjong_Tiles_(Unicode_block)
+        // Unicode: \U0001F005
+        BuildIconItem("\U0001F005", "Mahjong tile non-emoji (green dragon)", "Mahjong tile character that is not classified as an emoji"),
+
+        // Play, PlayPause, Stop
+        BuildIconItem("\u25B6", "Play symbol (standalone)", "Play symbol"),
+        BuildIconItem("\u25B6\uFE0E", "Play symbol + VS15 (request text)", "Play symbol with variation specifier requesting rendering as text"),
+        BuildIconItem("\u25B6\uFE0F", "Play symbol + VS16 (request emoji)", "Play symbol with variation specifier requesting rendering as emoji "),
+        BuildIconItem("⏯️", "Play/Pause keycap emoji", "Play/Pause keycap emoji doesn't have plain text variant"),
+        BuildIconItem("⏸️", "Pause keycap emoji", "Pause keycap emoji doesn't have plain text variant"),
+
+        // Copyright and emoji copyright:
+        BuildIconItem("\u00a9", "Copyright symbol (standalone)", "Copyright symbol that is not classified as an emoji"),
+        BuildIconItem("\u00a9\uFE0E", "Copyright symbol + VS15 (request text)", "Copyright symbol that is not classified as an emoji"),
+        BuildIconItem("\u00a9\uFE0F", "Copyright symbol + VS16 (request emoji)", "Copyright symbol that is not classified as an emoji"),
+
+        // Tag flags
+        BuildIconItem("🏳️", "White Flag", "White Flag"),
+        BuildIconItem("\U0001F3F4\u200D\u2620\uFE0F", "Pirate Flag", "Pirate Flag"),
+    ];
+
+    public SampleIconPage()
+    {
+        Icon = new IconInfo("\uE8BA");
+        Name = "Sample Icon Page";
+        ShowDetails = true;
+    }
+
+    public override IListItem[] GetItems() => _items;
+
+    private static ListItem BuildIconItem(string icon, string title, string description)
+    {
+        var iconInfo = new IconInfo(icon);
+
+        return new ListItem(new CopyTextCommand(icon) { Name = "Action with " + icon })
+        {
+            Title = title,
+            Subtitle = description,
+            Icon = iconInfo,
+            Tags = [
+                new Tag("Tag") { Icon = iconInfo },
+            ],
+            Details = new Details
+            {
+                HeroImage = iconInfo,
+                Title = title,
+                Body = description,
+                Metadata = [
+                    new DetailsElement
+                    {
+                        Key = "Unicode Code Points",
+                        Data = new DetailsTags
+                        {
+                            Tags = icon.EnumerateRunes()
+                                .Select(rune => rune.Value <= 0xFFFF ? $"\\u{rune.Value:X4}" : $"\\U{rune.Value:X8}")
+                                .Select(t => new Tag(t))
+                                .ToArray<ITag>(),
+                        },
+                    }
+                ],
+            },
+        };
+    }
+}

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

@@ -4,6 +4,7 @@
 
 using Microsoft.CommandPalette.Extensions;
 using Microsoft.CommandPalette.Extensions.Toolkit;
+using SamplePagesExtension.Pages;
 
 namespace SamplePagesExtension;
 
@@ -37,6 +38,11 @@ public partial class SamplesListPage : ListPage
             Title = "Demo of OnLoad/OnUnload",
             Subtitle = "Changes the list of items every time the page is opened / closed",
         },
+        new ListItem(new SampleIconPage())
+        {
+            Title = "Sample Icon Page",
+            Subtitle = "A demo of using icons in various ways",
+        },
 
         // Content pages
         new ListItem(new SampleContentPage())