chore(gitattributes): remove symlink entry for Claude Code support

<!-- Enter a brief description/summary of your PR here. What does it
fix/what does it change/how was it tested (even manually, if necessary)?
-->
## Summary of the Pull Request
Transparency support (best-effort)
> Not every window can be made transparent. Transparency is applied on a
best-effort basis and depends on how the target app/window is built and
rendered.

## When it may not work
* Windows with special rendering pipelines (e.g., certain
hardware-accelerated / compositor-managed surfaces).
* Some tool/popup/owned windows where the foreground window isn’t the
actual surface being drawn.

## How it works (high-level)
* Resolve the best target window (preferring the top-level/root window
over transient children).
* Apply Windows’ standard layered-window alpha mechanism (per-window
opacity) to adjust transparency.
* When unpinned, Restore the original opacity/state when possible.

If transparency doesn’t change, it means the window doesn’t support this
mechanism in its current configuration.
<!-- Please review the items on the PR checklist before submitting-->
## PR Checklist

- [X] Closes: 
#43278 
#42929
#28773

<!-- - [ ] Closes: #yyy (add separate lines for additional resolved
issues) -->
- [ ] **Communication:** I've discussed this with core contributors
already. If the work hasn't been agreed, this work might be rejected
- [ ] **Tests:** Added/updated and all pass
- [ ] **Localization:** All end-user-facing strings can be localized
- [ ] **Dev docs:** Added/updated
- [ ] **New binaries:** Added on the required places
- [ ] [JSON for
signing](https://github.com/microsoft/PowerToys/blob/main/.pipelines/ESRPSigning_core.json)
for new binaries
- [ ] [WXS for
installer](https://github.com/microsoft/PowerToys/blob/main/installer/PowerToysSetup/Product.wxs)
for new binaries and localization folder
- [ ] [YML for CI
pipeline](https://github.com/microsoft/PowerToys/blob/main/.pipelines/ci/templates/build-powertoys-steps.yml)
for new test projects
- [ ] [YML for signed
pipeline](https://github.com/microsoft/PowerToys/blob/main/.pipelines/release.yml)
- [ ] **Documentation updated:** If checked, please file a pull request
on [our docs
repo](https://github.com/MicrosoftDocs/windows-uwp/tree/docs/hub/powertoys)
and link it here: #xxx

<!-- Provide a more detailed description of the PR, other things fixed,
or any additional comments/features here -->
## Detailed Description of the Pull Request / Additional comments

<!-- Describe how you validated the behavior. Add automated tests
wherever possible, but list manual validation steps taken as well -->
## Validation Steps Performed


https://github.com/user-attachments/assets/c97a87f2-3126-4e19-990f-8c684dbeb631

<img width="1119" height="426" alt="image"
src="https://github.com/user-attachments/assets/547671ee-81d3-4c94-8199-bf0c4b1b7760"
/>

---------

Co-authored-by: Copilot <175728472+Copilot@users.noreply.github.com>

.claude/CLAUDE.md

@@ -0,0 +1 @@
+../.github/copilot-instructions.md

.claude/agents

@@ -0,0 +1 @@
+../.github/agents

.claude/commands

@@ -0,0 +1 @@
+../.github/prompts

.claude/rules

@@ -0,0 +1 @@
+../.github/instructions

.claude/skills

@@ -0,0 +1 @@
+../.github/skills

.github/actions/spell-check/candidate.patterns

@@ -565,7 +565,7 @@ perl(?:\s+-[a-zA-Z]\w*)+
 regexp?\.MustCompile\((?:`[^`]*`|".*"|'.*')\)
 
 # regex choice
-\(\?:[^)]+\|[^)]+\)
+# \(\?:[^)]+\|[^)]+\)
 
 # proto
 ^\s*(\w+)\s\g{-1} =

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

@@ -104,8 +104,12 @@
 ^src/common/ManagedCommon/ColorFormatHelper\.cs$
 ^src/common/notifications/BackgroundActivatorDLL/cpp\.hint$
 ^src/common/sysinternals/Eula/
+^src/modules/cmdpal/Tests/Microsoft\.CommandPalette\.Extensions\.Toolkit\.UnitTests/FuzzyMatcherComparisonTests.cs$
+^src/modules/cmdpal/Tests/Microsoft\.CommandPalette\.Extensions\.Toolkit\.UnitTests/FuzzyMatcherDiacriticsTests.cs$
 ^src/modules/cmdpal/doc/initial-sdk-spec/list-elements-mock-002\.pdn$
 ^src/modules/cmdpal/ext/SamplePagesExtension/Pages/SampleMarkdownImagesPage\.cs$
+^src/modules/cmdpal/Microsoft\.CmdPal\.UI/Settings/InternalPage\.SampleData\.cs$
+^src/modules/cmdpal/Tests/Microsoft\.CmdPal\.Core\.Common\.UnitTests/.*\.TestData\.cs$
 ^src/modules/colorPicker/ColorPickerUI/Shaders/GridShader\.cso$
 ^src/modules/launcher/Plugins/Microsoft\.PowerToys\.Run\.Plugin\.TimeDate/Properties/
 ^src/modules/MouseUtils/MouseJumpUI/MainForm\.resx$

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

@@ -22,7 +22,6 @@ ADate
 ADDSTRING
 ADDUNDORECORD
 ADifferent
-adjacents
 ADMINS
 adml
 admx
@@ -219,10 +218,11 @@ CIELCh
 cim
 CImage
 cla
-claude
 CLASSDC
+classguid
 classmethod
 CLASSNOTAVAILABLE
+claude
 CLEARTYPE
 clickable
 clickonce
@@ -261,7 +261,6 @@ colorhistory
 colorhistorylimit
 COLORKEY
 colorref
-Convs
 comctl
 comdlg
 comexp
@@ -282,6 +281,7 @@ CONTEXTHELP
 CONTEXTMENUHANDLER
 contractversion
 CONTROLPARENT
+Convs
 copiedcolorrepresentation
 coppied
 copyable
@@ -348,12 +348,14 @@ datareader
 datatracker
 dataversion
 Dayof
+dbcc
 DBID
 DBLCLKS
 DBLEPSILON
 DBPROP
 DBPROPIDSET
 DBPROPSET
+DBT
 DCBA
 DCOM
 DComposition
@@ -371,8 +373,7 @@ DEFAULTICON
 defaultlib
 DEFAULTONLY
 DEFAULTSIZE
-DEFAULTTONEAREST
-Defaulttonearest
+defaulttonearest
 DEFAULTTONULL
 DEFAULTTOPRIMARY
 DEFERERASE
@@ -394,14 +395,19 @@ DESKTOPVERTRES
 devblogs
 devdocs
 devenv
+DEVICEINTERFACE
+devicetype
+DEVINTERFACE
 devmgmt
 DEVMODE
 DEVMODEW
+DEVNODES
 devpal
+DEVTYP
 dfx
 DIALOGEX
-digicert
 diffs
+digicert
 DINORMAL
 DISABLEASACTIONKEY
 DISABLENOSCROLL
@@ -544,7 +550,6 @@ fdx
 FErase
 fesf
 FFFF
-FInc
 Figma
 FILEEXPLORER
 fileexploreraddons
@@ -565,6 +570,7 @@ FILESYSPATH
 Filetime
 FILEVERSION
 FILTERMODE
+FInc
 findfast
 findmymouse
 FIXEDFILEINFO
@@ -591,6 +597,7 @@ frm
 FROMTOUCH
 fsanitize
 fsmgmt
+ftps
 fuzzingtesting
 fxf
 FZE
@@ -666,13 +673,14 @@ HCRYPTPROV
 hcursor
 hcwhite
 hdc
+HDEVNOTIFY
 hdr
 hdrop
 hdwwiz
 Helpline
 helptext
-HGFE
 hgdiobj
+HGFE
 hglobal
 hhk
 HHmmssfff
@@ -748,9 +756,9 @@ HWNDPARENT
 HWNDPREV
 hyjiacan
 IAI
+icf
 ICONERROR
 ICONLOCATION
-icf
 IDCANCEL
 IDD
 idk
@@ -841,8 +849,8 @@ jeli
 jfif
 jgeosdfsdsgmkedfgdfgdfgbkmhcgcflmi
 jjw
-JOBOBJECT
 jobject
+JOBOBJECT
 jpe
 jpnime
 Jsons
@@ -929,9 +937,9 @@ LOWORD
 lparam
 LPBITMAPINFOHEADER
 LPCFHOOKPROC
+lpch
 LPCITEMIDLIST
 LPCLSID
-lpch
 lpcmi
 LPCMINVOKECOMMANDINFO
 LPCREATESTRUCT
@@ -947,6 +955,7 @@ LPMONITORINFO
 LPOSVERSIONINFOEXW
 LPQUERY
 lprc
+LPrivate
 LPSAFEARRAY
 lpstr
 lpsz
@@ -956,7 +965,6 @@ lptpm
 LPTR
 LPTSTR
 lpv
-LPrivate
 LPW
 lpwcx
 lpwndpl
@@ -1000,19 +1008,18 @@ mber
 MBM
 MBR
 Mbuttondown
+mcp
 MDICHILD
 MDL
 mdtext
 mdtxt
 mdwn
 meme
-mcp
 memicmp
 MENUITEMINFO
 MENUITEMINFOW
 MERGECOPY
 MERGEPAINT
-Metacharacter
 metadatamatters
 Metadatas
 metafile
@@ -1042,8 +1049,8 @@ mmi
 mmsys
 mobileredirect
 mockapi
-modelcontextprotocol
 MODALFRAME
+modelcontextprotocol
 MODESPRUNED
 MONITORENUMPROC
 MONITORINFO
@@ -1087,9 +1094,9 @@ MSLLHOOKSTRUCT
 Mso
 msrc
 msstore
+mstsc
 msvcp
 MT
-mstsc
 MTND
 MULTIPLEUSE
 multizone
@@ -1099,11 +1106,11 @@ muxxc
 muxxh
 MVPs
 mvvm
-myorg
-myrepo
 MVVMTK
 MWBEx
 MYICON
+myorg
+myrepo
 NAMECHANGE
 namespaceanddescendants
 nao
@@ -1244,10 +1251,8 @@ opencode
 OPENFILENAME
 openrdp
 opensource
-openxmlformats
-ollama
-onnx
 openurl
+openxmlformats
 OPTIMIZEFORINVOKE
 ORPHANEDDIALOGTITLE
 ORSCANS
@@ -1325,7 +1330,7 @@ phwnd
 pici
 pidl
 PIDLIST
-PII
+pii
 pinfo
 pinvoke
 pipename
@@ -1464,7 +1469,6 @@ rbhid
 Rbuttondown
 rclsid
 RCZOOMIT
-remotedesktop
 rdp
 RDW
 READMODE
@@ -1493,6 +1497,7 @@ remappings
 REMAPSUCCESSFUL
 REMAPUNSUCCESSFUL
 Remotable
+remotedesktop
 remoteip
 Removelnk
 renamable
@@ -1526,8 +1531,9 @@ RIGHTSCROLLBAR
 riid
 RKey
 RNumber
-rop
 rollups
+ROOTOWNER
+rop
 ROUNDSMALL
 ROWSETEXT
 rpcrt
@@ -1711,6 +1717,7 @@ srw
 srwlock
 sse
 ssf
+Ssn
 sszzz
 STACKFRAME
 stackoverflow
@@ -1766,8 +1773,7 @@ SVGIO
 svgz
 SVSI
 SWFO
-SWP
-Swp
+swp
 SWPNOSIZE
 SWPNOZORDER
 SWRESTORE
@@ -1786,8 +1792,7 @@ SYSKEY
 syskeydown
 SYSKEYUP
 SYSLIB
-SYSMENU
-Sysmenu
+sysmenu
 systemai
 SYSTEMAPPS
 SYSTEMMODAL
@@ -1822,6 +1827,7 @@ TEXTBOXNEWLINE
 textextractor
 TEXTINCLUDE
 tfopen
+tgamma
 tgz
 THEMECHANGED
 themeresources
@@ -1891,9 +1897,9 @@ uitests
 UITo
 ULONGLONG
 Ultrawide
-ums
 UMax
 UMin
+ums
 uncompilable
 UNCPRIORITY
 UNDNAME

.github/prompts/create-commit-title.prompt.md

@@ -1,6 +1,5 @@
 ---
 agent: 'agent'
-model: 'GPT-5.1-Codex-Max'
 description: 'Generate an 80-character git commit title for the local diff'
 ---
 

.github/prompts/create-pr-summary.prompt.md

@@ -1,6 +1,5 @@
 ---
 agent: 'agent'
-model: 'GPT-5.1-Codex-Max'
 description: 'Generate a PowerToys-ready pull request description from the local diff'
 ---
 

.github/prompts/fix-issue.prompt.md

@@ -1,6 +1,5 @@
 ---
 agent: 'agent'
-model: 'GPT-5.1-Codex-Max'
 description: 'Execute the fix for a GitHub issue using the previously generated implementation plan'
 ---
 

.github/prompts/fix-pr-active-comments.prompt.md

@@ -0,0 +1,70 @@
+---
+description: 'Fix active pull request comments with scoped changes'
+name: 'fix-pr-active-comments'
+agent: 'agent'
+argument-hint: 'PR number or active PR URL'
+---
+
+# Fix Active PR Comments
+
+## Mission
+Resolve active pull request comments by applying only simple fixes. For complex refactors, write a plan instead of changing code.
+
+## Scope & Preconditions
+- You must have an active pull request context or a provided PR number.
+- Only implement simple changes. Do not implement large refactors.
+- If required context is missing, request it and stop.
+
+## Inputs
+- Required: ${input:pr_number:PR number or URL}
+- Optional: ${input:comment_scope:files or areas to focus on}
+- Optional: ${input:fixing_guidelines:additional fixing guidelines from the user}
+
+## Workflow
+1. Locate all active (unresolved) PR review comments for the given PR.
+2. For each comment, classify the change scope:
+   - Simple change: limited edits, localized fix, low risk, no broad redesign.
+   - Large refactor: multi-file redesign, architecture change, or risky behavior change.
+3. For each large refactor request:
+   - Do not modify code.
+   - Write a planning document to Generated Files/prReview/${input:pr_number}/fixPlan/.
+4. For each simple change request:
+   - Implement the fix with minimal edits.
+   - Run quick checks if needed.
+   - Commit and push the change.
+5. For comments that seem invalid, unclear, or not applicable (even if simple):
+   - Do not change code.
+   - Add the item to a summary table in Generated Files/prReview/${input:pr_number}/fixPlan/overview.md.
+   - Consult back to the end user in a friendly, polite tone.
+6. Respond to each comment that you fixed:
+   - Reply in the active conversation.
+   - Use a polite or friendly tone.
+   - Keep the response under 200 words.
+   - Resolve the comment after replying.
+
+## Output Expectations
+- Simple fixes: code changes committed and pushed.
+- Large refactors: a plan file saved to Generated Files/prReview/${input:pr_number}/fixPlan/.
+- Invalid or unclear comments: captured in Generated Files/prReview/${input:pr_number}/fixPlan/overview.md.
+- Each fixed comment has a reply under 200 words and is resolved.
+
+## Plan File Template
+Use this template for each large refactor item:
+
+# Fix Plan: <short title>
+
+## Context
+- Comment link:
+- Impacted areas:
+
+## Overview Table Template
+Use this table in Generated Files/prReview/${input:pr_number}/fixPlan/overview.md:
+
+| Comment link | Summary | Reason not applied | Suggested follow-up |
+| --- | --- | --- | --- |
+|  |  |  |  |
+
+## Quality Assurance
+- Verify plan file path exists.
+- Ensure no code changes were made for large refactor items.
+- Confirm replies are under 200 words and comments are resolved.

.github/prompts/fix-spelling.prompt.md

@@ -1,6 +1,5 @@
 ---
 agent: 'agent'
-model: 'GPT-5.1-Codex-Max'
 description: 'Resolve Code scanning / check-spelling comments on the active PR'
 ---
 

.github/prompts/review-issue.prompt.md

@@ -1,6 +1,5 @@
 ---
 agent: 'agent'
-model: 'GPT-5.1-Codex-Max'
 description: 'Review a GitHub issue, score it (0-100), and generate an implementation plan'
 ---
 

.github/prompts/review-pr.prompt.md

@@ -1,6 +1,5 @@
 ---
 agent: 'agent'
-model: 'GPT-5.1-Codex-Max'
 description: 'Perform a comprehensive PR review with per-step Markdown and machine-readable outputs'
 ---
 

PowerToys.slnx

@@ -300,6 +300,10 @@
     </Project>
   </Folder>
   <Folder Name="/modules/CommandPalette/Tests/">
+    <Project Path="src/modules/cmdpal/Tests/Microsoft.CmdPal.Core.Common.UnitTests/Microsoft.CmdPal.Core.Common.UnitTests.csproj">
+      <Platform Solution="*|ARM64" Project="ARM64" />
+      <Platform Solution="*|x64" Project="x64" />
+    </Project>
     <Project Path="src/modules/cmdpal/Tests/Microsoft.CmdPal.Ext.Apps.UnitTests/Microsoft.CmdPal.Ext.Apps.UnitTests.csproj">
       <Platform Solution="*|ARM64" Project="ARM64" />
       <Platform Solution="*|x64" Project="x64" />
@@ -356,6 +360,10 @@
       <Platform Solution="*|ARM64" Project="ARM64" />
       <Platform Solution="*|x64" Project="x64" />
     </Project>
+    <Project Path="src/modules/cmdpal/Tests/Microsoft.CommandPalette.Extensions.Toolkit.UnitTests/Microsoft.CommandPalette.Extensions.Toolkit.UnitTests.csproj" Id="2eca18b7-33b7-4829-88f1-439b20fd60f6">
+      <Platform Solution="*|ARM64" Project="ARM64" />
+      <Platform Solution="*|x64" Project="x64" />
+    </Project>
   </Folder>
   <Folder Name="/modules/CommandPalette/UI/">
     <Project Path="src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Microsoft.CmdPal.UI.ViewModels.csproj">

README.md

@@ -51,19 +51,19 @@ But to get started quickly, choose one of the installation methods below:
 Go to the <a href="https://aka.ms/installPowerToys">PowerToys GitHub releases</a>, click Assets to reveal the downloads, and choose the installer that matches your architecture and install scope. For most devices, that's the x64 per-user installer.
 
 <!-- items that need to be updated release to release -->
-[github-next-release-work]: https://github.com/microsoft/PowerToys/issues?q=is%3Aissue+milestone%3A%22PowerToys+0.97%22
-[github-current-release-work]: https://github.com/microsoft/PowerToys/issues?q=is%3Aissue+milestone%3A%22PowerToys+0.96%22
-[ptUserX64]: https://github.com/microsoft/PowerToys/releases/download/v0.97.0/PowerToysUserSetup-0.97.0-x64.exe 
-[ptUserArm64]: https://github.com/microsoft/PowerToys/releases/download/v0.97.0/PowerToysUserSetup-0.97.0-arm64.exe 
-[ptMachineX64]: https://github.com/microsoft/PowerToys/releases/download/v0.97.0/PowerToysSetup-0.97.0-x64.exe 
-[ptMachineArm64]: https://github.com/microsoft/PowerToys/releases/download/v0.97.0/PowerToysSetup-0.97.0-arm64.exe
+[github-next-release-work]: https://github.com/microsoft/PowerToys/issues?q=is%3Aissue+milestone%3A%22PowerToys+0.98%22
+[github-current-release-work]: https://github.com/microsoft/PowerToys/issues?q=is%3Aissue+milestone%3A%22PowerToys+0.97%22
+[ptUserX64]: https://github.com/microsoft/PowerToys/releases/download/v0.97.1/PowerToysUserSetup-0.97.1-x64.exe 
+[ptUserArm64]: https://github.com/microsoft/PowerToys/releases/download/v0.97.1/PowerToysUserSetup-0.97.1-arm64.exe 
+[ptMachineX64]: https://github.com/microsoft/PowerToys/releases/download/v0.97.1/PowerToysSetup-0.97.1-x64.exe 
+[ptMachineArm64]: https://github.com/microsoft/PowerToys/releases/download/v0.97.1/PowerToysSetup-0.97.1-arm64.exe
  
 |  Description   | Filename |
 |----------------|----------|
-| Per user - x64       | [PowerToysUserSetup-0.97.0-x64.exe][ptUserX64] |
-| Per user - ARM64     | [PowerToysUserSetup-0.97.0-arm64.exe][ptUserArm64] |
-| Machine wide - x64   | [PowerToysSetup-0.97.0-x64.exe][ptMachineX64] |
-| Machine wide - ARM64 | [PowerToysSetup-0.97.0-arm64.exe][ptMachineArm64] |
+| Per user - x64       | [PowerToysUserSetup-0.97.1-x64.exe][ptUserX64] |
+| Per user - ARM64     | [PowerToysUserSetup-0.97.1-arm64.exe][ptUserArm64] |
+| Machine wide - x64   | [PowerToysSetup-0.97.1-x64.exe][ptMachineX64] |
+| Machine wide - ARM64 | [PowerToysSetup-0.97.1-arm64.exe][ptMachineArm64] |
 
 </details>
 
@@ -103,18 +103,38 @@ There are <a href="https://learn.microsoft.com/windows/powertoys/install#communi
 </details>
 
 ## ✨ What's new
-**Version 0.97 (January 2026)**
+**Version 0.97.1 (January 2026)**
 
-For an in-depth look at the latest changes, visit the [Windows Command Line blog](https://aka.ms/powertoys-releaseblog).
+This patch release fixes several important stability issues identified in v0.97.0 based on incoming reports. Check out the [v0.97.0](https://github.com/microsoft/PowerToys/releases/tag/v0.97.0) notes for the full list of changes.
 
-**✨ Highlights**
-- **Command Palette**: Major expansion with PowerToys extension (Windows 11 only), Remote Desktop built-in extension, theme customization, drag-and-drop support, fallback ranking controls, sections/separators for pages, pinyin Chinese matching, and many UX refinements.
-- **Settings**: Quick Access flyout is now a standalone process for significantly faster startup, theme-adaptive tray icon, AOT serialization, and multiple UI/accessibility fixes
-- **CursorWrap (New!)**: New mouse utility that lets your cursor wrap around screen edges, making multi-monitor navigation faster and more seamless.
-- **Advanced Paste**: Image input for AI, color detection in clipboard history, Foundry Local improvements, Azure AI icons, and multiple bug fixes
-- **CLI Support Expanded**: FancyZones, Image Resizer, and File Locksmith can now be controlled from the command line for layout management, batch image resizing, and file lock inspection.
-- **LightSwitch**: Added support for automatically following Windows Night Light mode.
-- **Release Experience & Quality**: Refreshed "What’s new" dialog, plus many performance improvements, stability fixes, and refinements across PowerToys.
+**Highlights**
+
+### Advanced Paste
+- #44862: Fixed Settings UI advanced paste page crash by using correct settings repository for null checking.
+
+### Command Palette
+- #44886: Fixed personalization section not appearing by using latest MSIX for installation.
+- #44938: Fixed loading of icons from internet shortcuts. Thanks [@jiripolasek](https://github.com/jiripolasek)!
+- #45076: Fixed potential deadlock from lazy-loading AppListItem details. Thanks [@jiripolasek](https://github.com/jiripolasek)!
+
+### Cursor Wrap
+- #44936: Added improved multi-monitor support; Added laptop lid close detection for dynamic monitor topology updates. Thanks [@mikehall-ms](https://github.com/mikehall-ms)!
+- #44936: Added new settings dropdown to constrain wrapping to horizontal-only, vertical-only, or both directions. Thanks [@mikehall-ms](https://github.com/mikehall-ms)!
+
+### Peek
+- #44995: Fixed Space key triggering Peek during file rename, search, or address bar typing.
+
+### PowerRename
+- #44944: Fixed regex `$` not working, preventing users from adding text at the end of filenames.
+
+### Runner
+- #44931: Monochrome tray icon now adapts to Windows system theme instead of app theme.
+- #44982: Fixed right-click menu to dynamically update based on Quick Access enabled/disabled state.
+
+### GPO / Enterprise
+- #45028: Added CursorWrap policy definition to ADMX templates. Thanks [@htcfreek](https://github.com/htcfreek)!
+
+For the full list of v0.97 changes, visit the [Windows Command Line blog](https://aka.ms/powertoys-releaseblog).
 
 ## Advanced Paste
 
@@ -289,7 +309,7 @@ For an in-depth look at the latest changes, visit the [Windows Command Line blog
 - Stabilized FancyZones UI tests with more reliable selectors and screen recordings.
 
 ## 🛣️ Roadmap 
-We are planning some nice new features and improvements for the next releases – PowerDisplay, Command Palette improvements and a brand-new Shortcut Guide experience! Stay tuned for [v0.97][github-next-release-work]!
+We are planning some nice new features and improvements for the next releases – PowerDisplay, Command Palette improvements and a brand-new Shortcut Guide experience! Stay tuned for [v0.98][github-next-release-work]!
 
 ## ❤️ PowerToys Community 
 The PowerToys team is extremely grateful to have the [support of an amazing active community][community-link]. The work you do is incredibly important. PowerToys wouldn't be nearly what it is today without your help filing bugs, updating documentation, guiding the design, or writing features. We want to say thank you and take time to recognize your work. Your contributions and feedback improve PowerToys month after month!

src/common/CalculatorEngineCommon/ExprtkEvaluator.cpp

@@ -3,9 +3,27 @@
 #include <iomanip>
 #include <iostream>
 #include <sstream>
+#include <cmath>
+#include <limits>
 
 namespace ExprtkCalculator::internal
 {
+    static double factorial(const double n)
+    {
+        // Only allow non-negative integers
+        if (n < 0.0 || std::floor(n) != n)
+        {
+            return std::numeric_limits<double>::quiet_NaN();
+        }
+        return std::tgamma(n + 1.0);
+    }
+
+    static double sign(const double n)
+    {
+        if (n > 0.0) return 1.0;
+        if (n < 0.0) return -1.0;
+        return 0.0;
+    }
 
     std::wstring ToWStringFullPrecision(double value)
     {
@@ -25,6 +43,9 @@ namespace ExprtkCalculator::internal
             symbol_table.add_constant(name, value);
         }
 
+        symbol_table.add_function("factorial", factorial);
+        symbol_table.add_function("sign", sign);
+
         exprtk::expression<double> expression;
         expression.register_symbol_table(symbol_table);
 

src/common/interop/shared_constants.h

@@ -72,6 +72,10 @@ namespace CommonSharedConstants
 
     const wchar_t ALWAYS_ON_TOP_TERMINATE_EVENT[] = L"Local\\AlwaysOnTopTerminateEvent-cfdf1eae-791f-4953-8021-2f18f3837eae";
 
+    const wchar_t ALWAYS_ON_TOP_INCREASE_OPACITY_EVENT[] = L"Local\\AlwaysOnTopIncreaseOpacityEvent-a1b2c3d4-e5f6-7890-abcd-ef1234567890";
+
+    const wchar_t ALWAYS_ON_TOP_DECREASE_OPACITY_EVENT[] = L"Local\\AlwaysOnTopDecreaseOpacityEvent-b2c3d4e5-f6a7-8901-bcde-f12345678901";
+
     // Path to the event used by PowerAccent
     const wchar_t POWERACCENT_EXIT_EVENT[] = L"Local\\PowerToysPowerAccentExitEvent-53e93389-d19a-4fbb-9b36-1981c8965e17";
 

src/gpo/assets/PowerToys.admx

@@ -1,11 +1,11 @@
 <?xml version="1.0" encoding="utf-8"?>
 <!-- Copyright (c) Microsoft Corporation.
      Licensed under the MIT License. -->
-<policyDefinitions xmlns:xsd="http://www.w3.org/2001/XMLSchema" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" revision="1.18" schemaVersion="1.0" xmlns="http://schemas.microsoft.com/GroupPolicy/2006/07/PolicyDefinitions">
+<policyDefinitions xmlns:xsd="http://www.w3.org/2001/XMLSchema" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" revision="1.19" schemaVersion="1.0" xmlns="http://schemas.microsoft.com/GroupPolicy/2006/07/PolicyDefinitions">
   <policyNamespaces>
     <target prefix="powertoys" namespace="Microsoft.Policies.PowerToys" />
   </policyNamespaces>
-  <resources minRequiredRevision="1.18"/><!-- Last changed with PowerToys v0.96.0 -->
+  <resources minRequiredRevision="1.19"/><!-- Last changed with PowerToys v0.97.0 -->
   <supportedOn>
     <definitions>
       <definition name="SUPPORTED_POWERTOYS_0_64_0" displayName="$(string.SUPPORTED_POWERTOYS_0_64_0)"/>
@@ -27,6 +27,7 @@
       <definition name="SUPPORTED_POWERTOYS_0_89_0" displayName="$(string.SUPPORTED_POWERTOYS_0_89_0)"/>
       <definition name="SUPPORTED_POWERTOYS_0_90_0" displayName="$(string.SUPPORTED_POWERTOYS_0_90_0)"/>
       <definition name="SUPPORTED_POWERTOYS_0_96_0" displayName="$(string.SUPPORTED_POWERTOYS_0_96_0)"/>
+      <definition name="SUPPORTED_POWERTOYS_0_97_0" displayName="$(string.SUPPORTED_POWERTOYS_0_97_0)"/>
       <definition name="SUPPORTED_POWERTOYS_0_64_0_TO_0_87_1" displayName="$(string.SUPPORTED_POWERTOYS_0_64_0_TO_0_87_1)"/>
     </definitions>
   </supportedOn>
@@ -338,6 +339,16 @@
         <decimal value="0" />
       </disabledValue>
     </policy>
+    <policy name="ConfigureEnabledUtilityCursorWrap" class="Both" displayName="$(string.ConfigureEnabledUtilityCursorWrap)" explainText="$(string.ConfigureEnabledUtilityDescription)" key="Software\Policies\PowerToys" valueName="ConfigureEnabledUtilityCursorWrap">
+      <parentCategory ref="PowerToys" />
+      <supportedOn ref="SUPPORTED_POWERTOYS_0_97_0" />
+      <enabledValue>
+        <decimal value="1" />
+      </enabledValue>
+      <disabledValue>
+        <decimal value="0" />
+      </disabledValue>
+    </policy>
     <policy name="ConfigureEnabledUtilityFindMyMouse" class="Both" displayName="$(string.ConfigureEnabledUtilityFindMyMouse)" explainText="$(string.ConfigureEnabledUtilityDescription)" key="Software\Policies\PowerToys" valueName="ConfigureEnabledUtilityFindMyMouse">
       <parentCategory ref="PowerToys" />
       <supportedOn ref="SUPPORTED_POWERTOYS_0_64_0" />

src/gpo/assets/en-US/PowerToys.adml

@@ -1,7 +1,7 @@
 <?xml version="1.0" encoding="utf-8"?>
 <!-- Copyright (c) Microsoft Corporation.
      Licensed under the MIT License. -->
-<policyDefinitionResources xmlns:xsd="http://www.w3.org/2001/XMLSchema" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" revision="1.18" schemaVersion="1.0" xmlns="http://schemas.microsoft.com/GroupPolicy/2006/07/PolicyDefinitions">
+<policyDefinitionResources xmlns:xsd="http://www.w3.org/2001/XMLSchema" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" revision="1.19" schemaVersion="1.0" xmlns="http://schemas.microsoft.com/GroupPolicy/2006/07/PolicyDefinitions">
   <displayName>PowerToys</displayName>
   <description>PowerToys</description>
   <resources>
@@ -34,6 +34,7 @@
       <string id="SUPPORTED_POWERTOYS_0_89_0">PowerToys version 0.89.0 or later</string>
       <string id="SUPPORTED_POWERTOYS_0_90_0">PowerToys version 0.90.0 or later</string>
       <string id="SUPPORTED_POWERTOYS_0_96_0">PowerToys version 0.96.0 or later</string>
+      <string id="SUPPORTED_POWERTOYS_0_97_0">PowerToys version 0.97.0 or later</string>
       <string id="SUPPORTED_POWERTOYS_0_64_0_TO_0_87_1">From PowerToys version 0.64.0 until PowerToys version 0.87.1</string>
 
       <string id="ConfigureAllUtilityGlobalEnabledStateDescription">This policy configures the enabled state for all PowerToys utilities.
@@ -266,6 +267,7 @@ If you don't configure this policy, the user will be able to control the setting
       <string id="ConfigureEnabledUtilityKeyboardManager">Keyboard Manager: Configure enabled state</string>
       <string id="ConfigureEnabledUtilityFindMyMouse">Find My Mouse: Configure enabled state</string>
       <string id="ConfigureEnabledUtilityMouseHighlighter">Mouse Highlighter: Configure enabled state</string>
+      <string id="ConfigureEnabledUtilityCursorWrap">CursorWrap: Configure enabled state</string>
       <string id="ConfigureEnabledUtilityMouseJump">Mouse Jump: Configure enabled state</string>
       <string id="ConfigureEnabledUtilityMousePointerCrosshairs">Mouse Pointer Crosshairs: Configure enabled state</string>
       <string id="ConfigureEnabledUtilityMouseWithoutBorders">Mouse Without Borders: Configure enabled state</string>

src/modules/MouseUtils/CursorWrap/CursorWrap.vcxproj

@@ -84,14 +84,17 @@
     </ClCompile>
   </ItemDefinitionGroup>
   <ItemGroup>
+    <ClInclude Include="CursorWrapCore.h" />
     <ClInclude Include="CursorWrapTests.h" />
+    <ClInclude Include="MonitorTopology.h" />
     <ClInclude Include="pch.h" />
     <ClInclude Include="trace.h" />
     <ClInclude Include="resource.h" />
   </ItemGroup>
   <ItemGroup>
+    <ClCompile Include="CursorWrapCore.cpp" />
     <ClCompile Include="dllmain.cpp" />
-
+    <ClCompile Include="MonitorTopology.cpp" />
     <ClCompile Include="pch.cpp">
       <PrecompiledHeader Condition="'$(UsePrecompiledHeaders)' != 'false'">Create</PrecompiledHeader>
     </ClCompile>

src/modules/MouseUtils/CursorWrap/CursorWrapCore.cpp

@@ -0,0 +1,268 @@
+// 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.
+
+#include "pch.h"
+#include "CursorWrapCore.h"
+#include "../../../common/logger/logger.h"
+#include <sstream>
+#include <iomanip>
+#include <ctime>
+
+CursorWrapCore::CursorWrapCore()
+{
+}
+
+#ifdef _DEBUG
+std::wstring CursorWrapCore::GenerateTopologyJSON() const
+{
+    std::wostringstream json;
+
+    // Get current time
+    auto now = std::time(nullptr);
+    std::tm tm{};
+    localtime_s(&tm, &now);
+
+    wchar_t computerName[MAX_COMPUTERNAME_LENGTH + 1] = {0};
+    DWORD size = MAX_COMPUTERNAME_LENGTH + 1;
+    GetComputerNameW(computerName, &size);
+
+    wchar_t userName[256] = {0};
+    size = 256;
+    GetUserNameW(userName, &size);
+
+    json << L"{\n";
+    json << L"  \"captured_at\": \"" << std::put_time(&tm, L"%Y-%m-%dT%H:%M:%S%z") << L"\",\n";
+    json << L"  \"computer_name\": \"" << computerName << L"\",\n";
+    json << L"  \"user_name\": \"" << userName << L"\",\n";
+    json << L"  \"monitor_count\": " << m_monitors.size() << L",\n";
+    json << L"  \"monitors\": [\n";
+
+    for (size_t i = 0; i < m_monitors.size(); ++i)
+    {
+        const auto& monitor = m_monitors[i];
+
+        // Get DPI for this monitor
+        UINT dpiX = 96, dpiY = 96;
+        POINT center = {
+            (monitor.rect.left + monitor.rect.right) / 2,
+            (monitor.rect.top + monitor.rect.bottom) / 2
+        };
+        HMONITOR hMon = MonitorFromPoint(center, MONITOR_DEFAULTTONEAREST);
+        if (hMon)
+        {
+            // Try GetDpiForMonitor (requires linking Shcore.lib)
+            using GetDpiForMonitorFunc = HRESULT (WINAPI *)(HMONITOR, int, UINT*, UINT*);
+            HMODULE shcore = LoadLibraryW(L"Shcore.dll");
+            if (shcore)
+            {
+                auto getDpi = reinterpret_cast<GetDpiForMonitorFunc>(GetProcAddress(shcore, "GetDpiForMonitor"));
+                if (getDpi)
+                {
+                    getDpi(hMon, 0, &dpiX, &dpiY); // MDT_EFFECTIVE_DPI = 0
+                }
+                FreeLibrary(shcore);
+            }
+        }
+
+        int scalingPercent = static_cast<int>((dpiX / 96.0) * 100);
+
+        json << L"    {\n";
+        json << L"      \"left\": " << monitor.rect.left << L",\n";
+        json << L"      \"top\": " << monitor.rect.top << L",\n";
+        json << L"      \"right\": " << monitor.rect.right << L",\n";
+        json << L"      \"bottom\": " << monitor.rect.bottom << L",\n";
+        json << L"      \"width\": " << (monitor.rect.right - monitor.rect.left) << L",\n";
+        json << L"      \"height\": " << (monitor.rect.bottom - monitor.rect.top) << L",\n";
+        json << L"      \"dpi\": " << dpiX << L",\n";
+        json << L"      \"scaling_percent\": " << scalingPercent << L",\n";
+        json << L"      \"primary\": " << (monitor.isPrimary ? L"true" : L"false") << L",\n";
+        json << L"      \"monitor_id\": " << monitor.monitorId << L"\n";
+        json << L"    }";
+        if (i < m_monitors.size() - 1)
+        {
+            json << L",";
+        }
+        json << L"\n";
+    }
+
+    json << L"  ]\n";
+    json << L"}";
+
+    return json.str();
+}
+#endif
+
+void CursorWrapCore::UpdateMonitorInfo()
+{
+    size_t previousMonitorCount = m_monitors.size();
+    Logger::info(L"======= UPDATE MONITOR INFO START =======");
+    Logger::info(L"Previous monitor count: {}", previousMonitorCount);
+
+    m_monitors.clear();
+
+    EnumDisplayMonitors(nullptr, nullptr, [](HMONITOR hMonitor, HDC, LPRECT, LPARAM lParam) -> BOOL {
+        auto* self = reinterpret_cast<CursorWrapCore*>(lParam);
+
+        MONITORINFO mi{};
+        mi.cbSize = sizeof(MONITORINFO);
+        if (GetMonitorInfo(hMonitor, &mi))
+        {
+            MonitorInfo info{};
+            info.hMonitor = hMonitor; // Store handle for direct comparison later
+            info.rect = mi.rcMonitor;
+            info.isPrimary = (mi.dwFlags & MONITORINFOF_PRIMARY) != 0;
+            info.monitorId = static_cast<int>(self->m_monitors.size());
+            self->m_monitors.push_back(info);
+            
+            Logger::info(L"Enumerated monitor {}: hMonitor={}, rect=({},{},{},{}), primary={}",
+                info.monitorId, reinterpret_cast<uintptr_t>(hMonitor),
+                mi.rcMonitor.left, mi.rcMonitor.top, mi.rcMonitor.right, mi.rcMonitor.bottom,
+                info.isPrimary ? L"yes" : L"no");
+        }
+
+        return TRUE;
+    }, reinterpret_cast<LPARAM>(this));
+
+    if (previousMonitorCount != m_monitors.size())
+    {
+        Logger::info(L"*** MONITOR CONFIGURATION CHANGED: {} -> {} monitors ***", 
+            previousMonitorCount, m_monitors.size());
+    }
+
+    m_topology.Initialize(m_monitors);
+
+    // Log monitor configuration summary
+    Logger::info(L"Monitor configuration updated: {} monitor(s)", m_monitors.size());
+    for (size_t i = 0; i < m_monitors.size(); ++i)
+    {
+        const auto& m = m_monitors[i];
+        int width = m.rect.right - m.rect.left;
+        int height = m.rect.bottom - m.rect.top;
+        Logger::info(L"  Monitor {}: {}x{} at ({}, {}){}",
+            i, width, height, m.rect.left, m.rect.top,
+            m.isPrimary ? L" [PRIMARY]" : L"");
+    }
+    Logger::info(L"  Detected {} outer edges for cursor wrapping", m_topology.GetOuterEdges().size());
+
+    // Detect and log monitor gaps
+    auto gaps = m_topology.DetectMonitorGaps();
+    if (!gaps.empty())
+    {
+        Logger::warn(L"Monitor configuration has coordinate gaps that may prevent wrapping:");
+        for (const auto& gap : gaps)
+        {
+            Logger::warn(L"  Gap between Monitor {} and Monitor {}: {}px horizontal gap, {}px vertical overlap",
+                gap.monitor1Index, gap.monitor2Index, gap.horizontalGap, gap.verticalOverlap);
+        }
+        Logger::warn(L"  If monitors appear snapped in Display Settings but show gaps here:");
+        Logger::warn(L"  1. Try dragging monitors apart and snapping them back together");
+        Logger::warn(L"  2. Update your GPU drivers");
+    }
+
+    Logger::info(L"======= UPDATE MONITOR INFO END =======");
+}
+
+POINT CursorWrapCore::HandleMouseMove(const POINT& currentPos, bool disableWrapDuringDrag, int wrapMode)
+{
+    // Check if wrapping should be disabled during drag
+    if (disableWrapDuringDrag && (GetAsyncKeyState(VK_LBUTTON) & 0x8000))
+    {
+#ifdef _DEBUG
+        OutputDebugStringW(L"[CursorWrap] [DRAG] Left mouse button down - skipping wrap\n");
+#endif
+        return currentPos;
+    }
+
+    // Convert int wrapMode to WrapMode enum
+    WrapMode mode = static_cast<WrapMode>(wrapMode);
+
+#ifdef _DEBUG
+    {
+        std::wostringstream oss;
+        oss << L"[CursorWrap] [MOVE] Cursor at (" << currentPos.x << L", " << currentPos.y << L")";
+
+        // Get current monitor and identify which one
+        HMONITOR currentMonitor = MonitorFromPoint(currentPos, MONITOR_DEFAULTTONEAREST);
+        RECT monitorRect;
+        if (m_topology.GetMonitorRect(currentMonitor, monitorRect))
+        {
+            // Find monitor ID
+            int monitorId = -1;
+            for (const auto& monitor : m_monitors)
+            {
+                if (monitor.rect.left == monitorRect.left &&
+                    monitor.rect.top == monitorRect.top &&
+                    monitor.rect.right == monitorRect.right &&
+                    monitor.rect.bottom == monitorRect.bottom)
+                {
+                    monitorId = monitor.monitorId;
+                    break;
+                }
+            }
+            oss << L" on Monitor " << monitorId << L" [" << monitorRect.left << L".." << monitorRect.right
+                << L", " << monitorRect.top << L".." << monitorRect.bottom << L"]";
+        }
+        else
+        {
+            oss << L" (beyond monitor bounds)";
+        }
+        oss << L"\n";
+        OutputDebugStringW(oss.str().c_str());
+    }
+#endif
+
+    // Get current monitor
+    HMONITOR currentMonitor = MonitorFromPoint(currentPos, MONITOR_DEFAULTTONEAREST);
+
+    // Check if cursor is on an outer edge (filtered by wrap mode)
+    EdgeType edgeType;
+    if (!m_topology.IsOnOuterEdge(currentMonitor, currentPos, edgeType, mode))
+    {
+#ifdef _DEBUG
+        static bool lastWasNotOuter = false;
+        if (!lastWasNotOuter)
+        {
+            OutputDebugStringW(L"[CursorWrap] [MOVE] Not on outer edge - no wrapping\n");
+            lastWasNotOuter = true;
+        }
+#endif
+        return currentPos; // Not on an outer edge
+    }
+
+#ifdef _DEBUG
+    {
+        const wchar_t* edgeStr = L"Unknown";
+        switch (edgeType)
+        {
+        case EdgeType::Left: edgeStr = L"Left"; break;
+        case EdgeType::Right: edgeStr = L"Right"; break;
+        case EdgeType::Top: edgeStr = L"Top"; break;
+        case EdgeType::Bottom: edgeStr = L"Bottom"; break;
+        }
+        std::wostringstream oss;
+        oss << L"[CursorWrap] [EDGE] Detected outer " << edgeStr << L" edge at (" << currentPos.x << L", " << currentPos.y << L")\n";
+        OutputDebugStringW(oss.str().c_str());
+    }
+#endif
+
+    // Calculate wrap destination
+    POINT newPos = m_topology.GetWrapDestination(currentMonitor, currentPos, edgeType);
+
+#ifdef _DEBUG
+    if (newPos.x != currentPos.x || newPos.y != currentPos.y)
+    {
+        std::wostringstream oss;
+        oss << L"[CursorWrap] [WRAP] Position change: (" << currentPos.x << L", " << currentPos.y
+            << L") -> (" << newPos.x << L", " << newPos.y << L")\n";
+        oss << L"[CursorWrap] [WRAP] Delta: (" << (newPos.x - currentPos.x) << L", " << (newPos.y - currentPos.y) << L")\n";
+        OutputDebugStringW(oss.str().c_str());
+    }
+    else
+    {
+        OutputDebugStringW(L"[CursorWrap] [WRAP] No position change (same-monitor wrap?)\n");
+    }
+#endif
+
+    return newPos;
+}

src/modules/MouseUtils/CursorWrap/CursorWrapCore.h

@@ -0,0 +1,33 @@
+// 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.
+
+#pragma once
+#include <windows.h>
+#include <vector>
+#include <string>
+#include "MonitorTopology.h"
+
+// Core cursor wrapping engine
+class CursorWrapCore
+{
+public:
+    CursorWrapCore();
+
+    void UpdateMonitorInfo();
+    
+    // Handle mouse move with wrap mode filtering
+    // wrapMode: 0=Both, 1=VerticalOnly, 2=HorizontalOnly
+    POINT HandleMouseMove(const POINT& currentPos, bool disableWrapDuringDrag, int wrapMode);
+
+    const std::vector<MonitorInfo>& GetMonitors() const { return m_monitors; }
+    const MonitorTopology& GetTopology() const { return m_topology; }
+
+private:
+#ifdef _DEBUG
+    std::wstring GenerateTopologyJSON() const;
+#endif
+
+    std::vector<MonitorInfo> m_monitors;
+    MonitorTopology m_topology;
+};

src/modules/MouseUtils/CursorWrap/MonitorTopology.cpp

@@ -0,0 +1,546 @@
+// 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.
+
+#include "pch.h"
+#include "MonitorTopology.h"
+#include "../../../common/logger/logger.h"
+#include <algorithm>
+#include <cmath>
+
+void MonitorTopology::Initialize(const std::vector<MonitorInfo>& monitors)
+{
+    Logger::info(L"======= TOPOLOGY INITIALIZATION START =======");
+    Logger::info(L"Initializing edge-based topology for {} monitors", monitors.size());
+
+    m_monitors = monitors;
+    m_outerEdges.clear();
+    m_edgeMap.clear();
+
+    if (monitors.empty())
+    {
+        Logger::warn(L"No monitors provided to Initialize");
+        return;
+    }
+
+    // Log monitor details
+    for (size_t i = 0; i < monitors.size(); ++i)
+    {
+        const auto& m = monitors[i];
+        Logger::info(L"Monitor {}: hMonitor={}, rect=({},{},{},{}), primary={}",
+            i, reinterpret_cast<uintptr_t>(m.hMonitor),
+            m.rect.left, m.rect.top, m.rect.right, m.rect.bottom,
+            m.isPrimary ? L"yes" : L"no");
+    }
+
+    BuildEdgeMap();
+    IdentifyOuterEdges();
+
+    Logger::info(L"Found {} outer edges", m_outerEdges.size());
+    for (const auto& edge : m_outerEdges)
+    {
+        const wchar_t* typeStr = L"Unknown";
+        switch (edge.type)
+        {
+        case EdgeType::Left: typeStr = L"Left"; break;
+        case EdgeType::Right: typeStr = L"Right"; break;
+        case EdgeType::Top: typeStr = L"Top"; break;
+        case EdgeType::Bottom: typeStr = L"Bottom"; break;
+        }
+        Logger::info(L"Outer edge: Monitor {} {} at position {}, range [{}, {}]",
+            edge.monitorIndex, typeStr, edge.position, edge.start, edge.end);
+    }
+    Logger::info(L"======= TOPOLOGY INITIALIZATION COMPLETE =======");
+}
+
+void MonitorTopology::BuildEdgeMap()
+{
+    // Create edges for each monitor using monitor index (not HMONITOR)
+    // This is important because HMONITOR handles can change when monitors are
+    // added/removed dynamically, but indices remain stable within a single
+    // topology configuration
+    for (size_t idx = 0; idx < m_monitors.size(); ++idx)
+    {
+        const auto& monitor = m_monitors[idx];
+        int monitorIndex = static_cast<int>(idx);
+
+        // Left edge
+        MonitorEdge leftEdge;
+        leftEdge.monitorIndex = monitorIndex;
+        leftEdge.type = EdgeType::Left;
+        leftEdge.position = monitor.rect.left;
+        leftEdge.start = monitor.rect.top;
+        leftEdge.end = monitor.rect.bottom;
+        leftEdge.isOuter = true; // Will be updated in IdentifyOuterEdges
+        m_edgeMap[{monitorIndex, EdgeType::Left}] = leftEdge;
+      
+        // Right edge
+        MonitorEdge rightEdge;
+        rightEdge.monitorIndex = monitorIndex;
+        rightEdge.type = EdgeType::Right;
+        rightEdge.position = monitor.rect.right - 1;
+        rightEdge.start = monitor.rect.top;
+        rightEdge.end = monitor.rect.bottom;
+        rightEdge.isOuter = true;
+        m_edgeMap[{monitorIndex, EdgeType::Right}] = rightEdge;
+
+        // Top edge
+        MonitorEdge topEdge;
+        topEdge.monitorIndex = monitorIndex;
+        topEdge.type = EdgeType::Top;
+        topEdge.position = monitor.rect.top;
+        topEdge.start = monitor.rect.left;
+        topEdge.end = monitor.rect.right;
+        topEdge.isOuter = true;
+        m_edgeMap[{monitorIndex, EdgeType::Top}] = topEdge;
+
+        // Bottom edge
+        MonitorEdge bottomEdge;
+        bottomEdge.monitorIndex = monitorIndex;
+        bottomEdge.type = EdgeType::Bottom;
+        bottomEdge.position = monitor.rect.bottom - 1;
+        bottomEdge.start = monitor.rect.left;
+        bottomEdge.end = monitor.rect.right;
+        bottomEdge.isOuter = true;
+        m_edgeMap[{monitorIndex, EdgeType::Bottom}] = bottomEdge;
+    }
+}
+
+void MonitorTopology::IdentifyOuterEdges()
+{
+    const int tolerance = 50;
+    
+    // Check each edge against all other edges to find adjacent ones
+    for (auto& [key1, edge1] : m_edgeMap)
+    {
+        for (const auto& [key2, edge2] : m_edgeMap)
+        {
+            if (edge1.monitorIndex == edge2.monitorIndex)
+            {
+                continue; // Same monitor
+            }
+
+            // Check if edges are adjacent
+            if (EdgesAreAdjacent(edge1, edge2, tolerance))
+            {
+                edge1.isOuter = false;
+                break; // This edge has an adjacent monitor
+            }
+        }
+
+        if (edge1.isOuter)
+        {
+            m_outerEdges.push_back(edge1);
+        }
+    }
+}
+
+bool MonitorTopology::EdgesAreAdjacent(const MonitorEdge& edge1, const MonitorEdge& edge2, int tolerance) const
+{
+    // Edges must be opposite types to be adjacent
+    bool oppositeTypes = false;
+
+    if ((edge1.type == EdgeType::Left && edge2.type == EdgeType::Right) ||
+        (edge1.type == EdgeType::Right && edge2.type == EdgeType::Left) ||
+        (edge1.type == EdgeType::Top && edge2.type == EdgeType::Bottom) ||
+        (edge1.type == EdgeType::Bottom && edge2.type == EdgeType::Top))
+    {
+        oppositeTypes = true;
+    }
+
+    if (!oppositeTypes)
+    {
+        return false;
+    }
+
+    // Check if positions are within tolerance
+    if (abs(edge1.position - edge2.position) > tolerance)
+    {
+        return false;
+    }
+
+    // Check if perpendicular ranges overlap
+    int overlapStart = max(edge1.start, edge2.start);
+    int overlapEnd = min(edge1.end, edge2.end);
+
+    return overlapEnd > overlapStart + tolerance;
+}
+
+bool MonitorTopology::IsOnOuterEdge(HMONITOR monitor, const POINT& cursorPos, EdgeType& outEdgeType, WrapMode wrapMode) const
+{
+    RECT monitorRect;
+    if (!GetMonitorRect(monitor, monitorRect))
+    {
+        Logger::warn(L"IsOnOuterEdge: GetMonitorRect failed for monitor handle {}", reinterpret_cast<uintptr_t>(monitor));
+        return false;
+    }
+
+    // Get monitor index for edge map lookup
+    int monitorIndex = GetMonitorIndex(monitor);
+    if (monitorIndex < 0)
+    {
+        Logger::warn(L"IsOnOuterEdge: Monitor index not found for handle {} at cursor ({}, {})", 
+            reinterpret_cast<uintptr_t>(monitor), cursorPos.x, cursorPos.y);
+        return false; // Monitor not found in our list
+    }
+
+    // Check each edge type
+    const int edgeThreshold = 1;
+
+    // At corners, multiple edges may match - collect all candidates and try each
+    // to find one with a valid wrap destination
+    std::vector<EdgeType> candidateEdges;
+
+    // Left edge - only if mode allows horizontal wrapping
+    if ((wrapMode == WrapMode::Both || wrapMode == WrapMode::HorizontalOnly) &&
+        cursorPos.x <= monitorRect.left + edgeThreshold)
+    {
+        auto it = m_edgeMap.find({monitorIndex, EdgeType::Left});
+        if (it != m_edgeMap.end() && it->second.isOuter)
+        {
+            candidateEdges.push_back(EdgeType::Left);
+        }
+    }
+
+    // Right edge - only if mode allows horizontal wrapping
+    if ((wrapMode == WrapMode::Both || wrapMode == WrapMode::HorizontalOnly) &&
+        cursorPos.x >= monitorRect.right - 1 - edgeThreshold)
+    {
+        auto it = m_edgeMap.find({monitorIndex, EdgeType::Right});
+        if (it != m_edgeMap.end())
+        {
+            if (it->second.isOuter)
+            {
+                candidateEdges.push_back(EdgeType::Right);
+            }
+            // Debug: Log why right edge isn't outer
+            else
+            {
+                Logger::trace(L"IsOnOuterEdge: Monitor {} right edge is NOT outer (inner edge)", monitorIndex);
+            }
+        }
+    }
+
+    // Top edge - only if mode allows vertical wrapping
+    if ((wrapMode == WrapMode::Both || wrapMode == WrapMode::VerticalOnly) &&
+        cursorPos.y <= monitorRect.top + edgeThreshold)
+    {
+        auto it = m_edgeMap.find({monitorIndex, EdgeType::Top});
+        if (it != m_edgeMap.end() && it->second.isOuter)
+        {
+            candidateEdges.push_back(EdgeType::Top);
+        }
+    }
+
+    // Bottom edge - only if mode allows vertical wrapping
+    if ((wrapMode == WrapMode::Both || wrapMode == WrapMode::VerticalOnly) &&
+        cursorPos.y >= monitorRect.bottom - 1 - edgeThreshold)
+    {
+        auto it = m_edgeMap.find({monitorIndex, EdgeType::Bottom});
+        if (it != m_edgeMap.end() && it->second.isOuter)
+        {
+            candidateEdges.push_back(EdgeType::Bottom);
+        }
+    }
+
+    if (candidateEdges.empty())
+    {
+        return false;
+    }
+
+    // Try each candidate edge and return first with valid wrap destination
+    for (EdgeType candidate : candidateEdges)
+    {
+        MonitorEdge oppositeEdge = FindOppositeOuterEdge(candidate,
+            (candidate == EdgeType::Left || candidate == EdgeType::Right) ? cursorPos.y : cursorPos.x);
+
+        if (oppositeEdge.monitorIndex >= 0)
+        {
+            outEdgeType = candidate;
+            return true;
+        }
+    }
+
+    return false;
+}
+
+POINT MonitorTopology::GetWrapDestination(HMONITOR fromMonitor, const POINT& cursorPos, EdgeType edgeType) const
+{
+    // Get monitor index for edge map lookup
+    int monitorIndex = GetMonitorIndex(fromMonitor);
+    if (monitorIndex < 0)
+    {
+        return cursorPos; // Monitor not found
+    }
+
+    auto it = m_edgeMap.find({monitorIndex, edgeType});
+    if (it == m_edgeMap.end())
+    {
+        return cursorPos; // Edge not found
+    }
+
+    const MonitorEdge& fromEdge = it->second;
+
+    // Calculate relative position on current edge (0.0 to 1.0)
+    double relativePos = GetRelativePosition(fromEdge,
+        (edgeType == EdgeType::Left || edgeType == EdgeType::Right) ? cursorPos.y : cursorPos.x);
+
+    // Find opposite outer edge
+    MonitorEdge oppositeEdge = FindOppositeOuterEdge(edgeType,
+        (edgeType == EdgeType::Left || edgeType == EdgeType::Right) ? cursorPos.y : cursorPos.x);
+
+    if (oppositeEdge.monitorIndex < 0)
+    {
+        // No opposite edge found, wrap within same monitor
+        RECT monitorRect;
+        if (GetMonitorRect(fromMonitor, monitorRect))
+        {
+            POINT result = cursorPos;
+            switch (edgeType)
+            {
+            case EdgeType::Left:
+                result.x = monitorRect.right - 2;
+                break;
+            case EdgeType::Right:
+                result.x = monitorRect.left + 1;
+                break;
+            case EdgeType::Top:
+                result.y = monitorRect.bottom - 2;
+                break;
+            case EdgeType::Bottom:
+                result.y = monitorRect.top + 1;
+                break;
+            }
+            return result;
+        }
+        return cursorPos;
+    }
+
+    // Calculate target position on opposite edge
+    POINT result;
+
+    if (edgeType == EdgeType::Left || edgeType == EdgeType::Right)
+    {
+        // Horizontal edge -> vertical movement
+        result.x = oppositeEdge.position;
+        result.y = GetAbsolutePosition(oppositeEdge, relativePos);
+    }
+    else
+    {
+        // Vertical edge -> horizontal movement
+        result.y = oppositeEdge.position;
+        result.x = GetAbsolutePosition(oppositeEdge, relativePos);
+    }
+
+    return result;
+}
+
+MonitorEdge MonitorTopology::FindOppositeOuterEdge(EdgeType fromEdge, int relativePosition) const
+{
+    EdgeType targetType;
+    bool findMax; // true = find max position, false = find min position
+
+    switch (fromEdge)
+    {
+    case EdgeType::Left:
+        targetType = EdgeType::Right;
+        findMax = true;
+        break;
+    case EdgeType::Right:
+        targetType = EdgeType::Left;
+        findMax = false;
+        break;
+    case EdgeType::Top:
+        targetType = EdgeType::Bottom;
+        findMax = true;
+        break;
+    case EdgeType::Bottom:
+        targetType = EdgeType::Top;
+        findMax = false;
+        break;
+    default:
+        return { .monitorIndex = -1 }; // Invalid edge type
+    }
+
+    MonitorEdge result = { .monitorIndex = -1 }; // -1 indicates not found
+    int extremePosition = findMax ? INT_MIN : INT_MAX;
+
+    for (const auto& edge : m_outerEdges)
+    {
+        if (edge.type != targetType)
+        {
+            continue;
+        }
+
+        // Check if this edge overlaps with the relative position
+        if (relativePosition >= edge.start && relativePosition <= edge.end)
+        {
+            if ((findMax && edge.position > extremePosition) ||
+                (!findMax && edge.position < extremePosition))
+            {
+                extremePosition = edge.position;
+                result = edge;
+            }
+        }
+    }
+
+    return result;
+}
+
+double MonitorTopology::GetRelativePosition(const MonitorEdge& edge, int coordinate) const
+{
+    if (edge.end == edge.start)
+    {
+        return 0.5; // Avoid division by zero
+    }
+
+    int clamped = max(edge.start, min(coordinate, edge.end));
+    // Use int64_t to avoid overflow warning C26451
+    int64_t numerator = static_cast<int64_t>(clamped) - static_cast<int64_t>(edge.start);
+    int64_t denominator = static_cast<int64_t>(edge.end) - static_cast<int64_t>(edge.start);
+    return static_cast<double>(numerator) / static_cast<double>(denominator);
+}
+
+int MonitorTopology::GetAbsolutePosition(const MonitorEdge& edge, double relativePosition) const
+{
+    // Use int64_t to prevent arithmetic overflow during subtraction and multiplication
+    int64_t range = static_cast<int64_t>(edge.end) - static_cast<int64_t>(edge.start);
+    int64_t offset = static_cast<int64_t>(relativePosition * static_cast<double>(range));
+    // Clamp result to int range before returning
+    int64_t result = static_cast<int64_t>(edge.start) + offset;
+    return static_cast<int>(result);
+}
+
+std::vector<MonitorTopology::GapInfo> MonitorTopology::DetectMonitorGaps() const
+{
+    std::vector<GapInfo> gaps;
+    const int gapThreshold = 50; // Same as ADJACENCY_TOLERANCE
+
+    // Check each pair of monitors
+    for (size_t i = 0; i < m_monitors.size(); ++i)
+    {
+        for (size_t j = i + 1; j < m_monitors.size(); ++j)
+        {
+            const auto& m1 = m_monitors[i];
+            const auto& m2 = m_monitors[j];
+
+            // Check vertical overlap
+            int vOverlapStart = max(m1.rect.top, m2.rect.top);
+            int vOverlapEnd = min(m1.rect.bottom, m2.rect.bottom);
+            int vOverlap = vOverlapEnd - vOverlapStart;
+
+            if (vOverlap <= 0)
+            {
+                continue; // No vertical overlap, skip
+            }
+
+            // Check horizontal gap
+            int hGap = min(abs(m1.rect.right - m2.rect.left), abs(m2.rect.right - m1.rect.left));
+
+            if (hGap > gapThreshold)
+            {
+                GapInfo gap;
+                gap.monitor1Index = static_cast<int>(i);
+                gap.monitor2Index = static_cast<int>(j);
+                gap.horizontalGap = hGap;
+                gap.verticalOverlap = vOverlap;
+                gaps.push_back(gap);
+            }
+        }
+    }
+
+    return gaps;
+}
+
+HMONITOR MonitorTopology::GetMonitorFromPoint(const POINT& pt) const
+{
+    return MonitorFromPoint(pt, MONITOR_DEFAULTTONEAREST);
+}
+
+bool MonitorTopology::GetMonitorRect(HMONITOR monitor, RECT& rect) const
+{
+    // First try direct HMONITOR comparison
+    for (const auto& monitorInfo : m_monitors)
+    {
+        if (monitorInfo.hMonitor == monitor)
+        {
+            rect = monitorInfo.rect;
+            return true;
+        }
+    }
+
+    // Fallback: If direct comparison fails, try matching by current monitor info
+    MONITORINFO mi{};
+    mi.cbSize = sizeof(MONITORINFO);
+    if (GetMonitorInfo(monitor, &mi))
+    {
+        for (const auto& monitorInfo : m_monitors)
+        {
+            if (monitorInfo.rect.left == mi.rcMonitor.left &&
+                monitorInfo.rect.top == mi.rcMonitor.top &&
+                monitorInfo.rect.right == mi.rcMonitor.right &&
+                monitorInfo.rect.bottom == mi.rcMonitor.bottom)
+            {
+                rect = monitorInfo.rect;
+                return true;
+            }
+        }
+    }
+    
+    return false;
+}
+
+HMONITOR MonitorTopology::GetMonitorFromRect(const RECT& rect) const
+{
+    return MonitorFromRect(&rect, MONITOR_DEFAULTTONEAREST);
+}
+
+int MonitorTopology::GetMonitorIndex(HMONITOR monitor) const
+{
+    // First try direct HMONITOR comparison (fast and accurate)
+    for (size_t i = 0; i < m_monitors.size(); ++i)
+    {
+        if (m_monitors[i].hMonitor == monitor)
+        {
+            return static_cast<int>(i);
+        }
+    }
+
+    // Fallback: If direct comparison fails (e.g., handle changed after display reconfiguration),
+    // try matching by position. Get the monitor's current rect and find matching stored rect.
+    MONITORINFO mi{};
+    mi.cbSize = sizeof(MONITORINFO);
+    if (GetMonitorInfo(monitor, &mi))
+    {
+        for (size_t i = 0; i < m_monitors.size(); ++i)
+        {
+            // Match by rect bounds
+            if (m_monitors[i].rect.left == mi.rcMonitor.left &&
+                m_monitors[i].rect.top == mi.rcMonitor.top &&
+                m_monitors[i].rect.right == mi.rcMonitor.right &&
+                m_monitors[i].rect.bottom == mi.rcMonitor.bottom)
+            {
+                Logger::trace(L"GetMonitorIndex: Found monitor {} via rect fallback (handle changed from {} to {})", 
+                    i, reinterpret_cast<uintptr_t>(m_monitors[i].hMonitor), reinterpret_cast<uintptr_t>(monitor));
+                return static_cast<int>(i);
+            }
+        }
+        
+        // Log all stored monitors vs the requested one for debugging
+        Logger::warn(L"GetMonitorIndex: No match found. Requested monitor rect=({},{},{},{})",
+            mi.rcMonitor.left, mi.rcMonitor.top, mi.rcMonitor.right, mi.rcMonitor.bottom);
+        for (size_t i = 0; i < m_monitors.size(); ++i)
+        {
+            Logger::warn(L"  Stored monitor {}: rect=({},{},{},{})",
+                i, m_monitors[i].rect.left, m_monitors[i].rect.top, 
+                m_monitors[i].rect.right, m_monitors[i].rect.bottom);
+        }
+    }
+    else
+    {
+        Logger::warn(L"GetMonitorIndex: GetMonitorInfo failed for handle {}", reinterpret_cast<uintptr_t>(monitor));
+    }
+
+    return -1; // Not found
+}
+

src/modules/MouseUtils/CursorWrap/MonitorTopology.h

@@ -0,0 +1,106 @@
+// 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.
+
+#pragma once
+#include <windows.h>
+#include <vector>
+#include <map>
+
+// Monitor information structure
+struct MonitorInfo
+{
+    HMONITOR hMonitor; // Direct handle for accurate lookup after display changes
+    RECT rect;
+    bool isPrimary;
+    int monitorId;
+};
+
+// Edge type enumeration
+enum class EdgeType
+{
+    Left = 0,
+    Right = 1,
+    Top = 2,
+    Bottom = 3
+};
+
+// Wrap mode enumeration (matches Settings UI dropdown)
+enum class WrapMode
+{
+    Both = 0,           // Wrap in both directions
+    VerticalOnly = 1,   // Only wrap top/bottom
+    HorizontalOnly = 2  // Only wrap left/right
+};
+
+// Represents a single edge of a monitor
+struct MonitorEdge
+{
+    int monitorIndex;  // Index into m_monitors (stable across display changes)
+    EdgeType type;
+    int start;      // For vertical edges: Y start; horizontal: X start
+    int end;        // For vertical edges: Y end; horizontal: X end
+    int position;   // For vertical edges: X coord; horizontal: Y coord
+    bool isOuter;   // True if no adjacent monitor touches this edge
+};
+
+// Monitor topology helper - manages edge-based monitor layout
+struct MonitorTopology
+{
+    void Initialize(const std::vector<MonitorInfo>& monitors);
+
+    // Check if cursor is on an outer edge of the given monitor
+    // wrapMode filters which edges are considered (Both, VerticalOnly, HorizontalOnly)
+    bool IsOnOuterEdge(HMONITOR monitor, const POINT& cursorPos, EdgeType& outEdgeType, WrapMode wrapMode) const;
+
+    // Get the wrap destination point for a cursor on an outer edge
+    POINT GetWrapDestination(HMONITOR fromMonitor, const POINT& cursorPos, EdgeType edgeType) const;
+
+    // Get monitor at point (helper)
+    HMONITOR GetMonitorFromPoint(const POINT& pt) const;
+
+    // Get monitor rectangle (helper)
+    bool GetMonitorRect(HMONITOR monitor, RECT& rect) const;
+
+    // Get outer edges collection (for debugging)
+    const std::vector<MonitorEdge>& GetOuterEdges() const { return m_outerEdges; }
+
+    // Detect gaps between monitors that should be snapped together
+    struct GapInfo {
+        int monitor1Index;
+        int monitor2Index;
+        int horizontalGap;
+        int verticalOverlap;
+    };
+    std::vector<GapInfo> DetectMonitorGaps() const;
+
+private:
+    std::vector<MonitorInfo> m_monitors;
+    std::vector<MonitorEdge> m_outerEdges;
+
+    // Map from (monitor index, edge type) to edge info
+    // Using monitor index instead of HMONITOR because HMONITOR handles can change
+    // when monitors are added/removed dynamically
+    std::map<std::pair<int, EdgeType>, MonitorEdge> m_edgeMap;
+
+    // Helper to resolve HMONITOR to monitor index at runtime
+    int GetMonitorIndex(HMONITOR monitor) const;
+
+    // Helper to get consistent HMONITOR from RECT
+    HMONITOR GetMonitorFromRect(const RECT& rect) const;
+    
+    void BuildEdgeMap();
+    void IdentifyOuterEdges();
+
+    // Check if two edges are adjacent (within tolerance)
+    bool EdgesAreAdjacent(const MonitorEdge& edge1, const MonitorEdge& edge2, int tolerance = 50) const;
+
+    // Find the opposite outer edge for wrapping
+    MonitorEdge FindOppositeOuterEdge(EdgeType fromEdge, int relativePosition) const;
+
+    // Calculate relative position along an edge (0.0 to 1.0)
+    double GetRelativePosition(const MonitorEdge& edge, int coordinate) const;
+
+    // Convert relative position to absolute coordinate on target edge
+    int GetAbsolutePosition(const MonitorEdge& edge, double relativePosition) const;
+};

src/modules/alwaysontop/AlwaysOnTop/AlwaysOnTop.cpp

@@ -153,9 +153,21 @@ LRESULT AlwaysOnTop::WndProc(HWND window, UINT message, WPARAM wparam, LPARAM lp
 {
     if (message == WM_HOTKEY)
     {
+        int hotkeyId = static_cast<int>(wparam);
         if (HWND fw{ GetForegroundWindow() })
         {
-            ProcessCommand(fw);
+            if (hotkeyId == static_cast<int>(HotkeyId::Pin))
+            {
+                ProcessCommand(fw);
+            }
+            else if (hotkeyId == static_cast<int>(HotkeyId::IncreaseOpacity))
+            {
+                StepWindowTransparency(fw, Settings::transparencyStep);
+            }
+            else if (hotkeyId == static_cast<int>(HotkeyId::DecreaseOpacity))
+            {
+                StepWindowTransparency(fw, -Settings::transparencyStep);
+            }
         }
     }
     else if (message == WM_PRIV_SETTINGS_CHANGED)
@@ -191,6 +203,10 @@ void AlwaysOnTop::ProcessCommand(HWND window)
                 m_topmostWindows.erase(iter);
             }
 
+            // Restore transparency when unpinning
+            RestoreWindowAlpha(window);
+            m_windowOriginalLayeredState.erase(window);
+
             Trace::AlwaysOnTop::UnpinWindow();
         }
     }
@@ -200,6 +216,7 @@ void AlwaysOnTop::ProcessCommand(HWND window)
         {
             soundType = Sound::Type::On;
             AssignBorder(window);
+            
             Trace::AlwaysOnTop::PinWindow();
         }
     }
@@ -269,11 +286,22 @@ void AlwaysOnTop::RegisterHotkey() const
 {
     if (m_useCentralizedLLKH)
     {
+        // All hotkeys are handled by centralized LLKH
         return;
     }
 
+    // Register hotkeys only when not using centralized LLKH
     UnregisterHotKey(m_window, static_cast<int>(HotkeyId::Pin));
+    UnregisterHotKey(m_window, static_cast<int>(HotkeyId::IncreaseOpacity));
+    UnregisterHotKey(m_window, static_cast<int>(HotkeyId::DecreaseOpacity));
+
+    // Register pin hotkey
     RegisterHotKey(m_window, static_cast<int>(HotkeyId::Pin), AlwaysOnTopSettings::settings().hotkey.get_modifiers(), AlwaysOnTopSettings::settings().hotkey.get_code());
+
+    // Register transparency hotkeys using the same modifiers as the pin hotkey
+    UINT modifiers = AlwaysOnTopSettings::settings().hotkey.get_modifiers();
+    RegisterHotKey(m_window, static_cast<int>(HotkeyId::IncreaseOpacity), modifiers, VK_OEM_PLUS);
+    RegisterHotKey(m_window, static_cast<int>(HotkeyId::DecreaseOpacity), modifiers, VK_OEM_MINUS);
 }
 
 void AlwaysOnTop::RegisterLLKH()
@@ -285,6 +313,8 @@ void AlwaysOnTop::RegisterLLKH()
 	
     m_hPinEvent = CreateEventW(nullptr, false, false, CommonSharedConstants::ALWAYS_ON_TOP_PIN_EVENT);
     m_hTerminateEvent = CreateEventW(nullptr, false, false, CommonSharedConstants::ALWAYS_ON_TOP_TERMINATE_EVENT);
+    m_hIncreaseOpacityEvent = CreateEventW(nullptr, false, false, CommonSharedConstants::ALWAYS_ON_TOP_INCREASE_OPACITY_EVENT);
+    m_hDecreaseOpacityEvent = CreateEventW(nullptr, false, false, CommonSharedConstants::ALWAYS_ON_TOP_DECREASE_OPACITY_EVENT);
 
     if (!m_hPinEvent)
     {
@@ -298,30 +328,54 @@ void AlwaysOnTop::RegisterLLKH()
         return;
     }
 
-    HANDLE handles[2] = { m_hPinEvent,
-                          m_hTerminateEvent };
+    if (!m_hIncreaseOpacityEvent)
+    {
+        Logger::warn(L"Failed to create increaseOpacityEvent. {}", get_last_error_or_default(GetLastError()));
+    }
+
+    if (!m_hDecreaseOpacityEvent)
+    {
+        Logger::warn(L"Failed to create decreaseOpacityEvent. {}", get_last_error_or_default(GetLastError()));
+    }
+
+    HANDLE handles[4] = { m_hPinEvent,
+                          m_hTerminateEvent,
+                          m_hIncreaseOpacityEvent,
+                          m_hDecreaseOpacityEvent };
 
     m_thread = std::thread([this, handles]() {
         MSG msg;
         while (m_running)
         {
-            DWORD dwEvt = MsgWaitForMultipleObjects(2, handles, false, INFINITE, QS_ALLINPUT);
+            DWORD dwEvt = MsgWaitForMultipleObjects(4, handles, false, INFINITE, QS_ALLINPUT);
             if (!m_running)
             {
                 break;
             }
             switch (dwEvt)
             {
-            case WAIT_OBJECT_0:
+            case WAIT_OBJECT_0: // Pin event
                 if (HWND fw{ GetForegroundWindow() })
                 {
                     ProcessCommand(fw);
                 }
                 break;
-            case WAIT_OBJECT_0 + 1:
+            case WAIT_OBJECT_0 + 1: // Terminate event
                 PostThreadMessage(m_mainThreadId, WM_QUIT, 0, 0);
                 break;
-            case WAIT_OBJECT_0 + 2:
+            case WAIT_OBJECT_0 + 2: // Increase opacity event
+                if (HWND fw{ GetForegroundWindow() })
+                {
+                    StepWindowTransparency(fw, Settings::transparencyStep);
+                }
+                break;
+            case WAIT_OBJECT_0 + 3: // Decrease opacity event
+                if (HWND fw{ GetForegroundWindow() })
+                {
+                    StepWindowTransparency(fw, -Settings::transparencyStep);
+                }
+                break;
+            case WAIT_OBJECT_0 + 4: // Message queue
                 if (PeekMessageW(&msg, nullptr, 0, 0, PM_REMOVE))
                 {
                     TranslateMessage(&msg);
@@ -370,9 +424,12 @@ void AlwaysOnTop::UnpinAll()
         {
             Logger::error(L"Unpinning topmost window failed");
         }
+        // Restore transparency when unpinning all
+        RestoreWindowAlpha(topWindow);
     }
 
     m_topmostWindows.clear();
+    m_windowOriginalLayeredState.clear();
 }
 
 void AlwaysOnTop::CleanUp()
@@ -456,6 +513,7 @@ void AlwaysOnTop::HandleWinHookEvent(WinHookEvent* data) noexcept
     for (const auto window : toErase)
     {
         m_topmostWindows.erase(window);
+        m_windowOriginalLayeredState.erase(window);
     }
 
     switch (data->event)
@@ -556,4 +614,166 @@ void AlwaysOnTop::RefreshBorders()
             }
         }
     }
+}
+
+HWND AlwaysOnTop::ResolveTransparencyTargetWindow(HWND window)
+{
+    if (!window || !IsWindow(window))
+    {
+        return nullptr;
+    }
+
+    // Only allow transparency changes on pinned windows
+    if (!IsPinned(window))
+    {
+        return nullptr;
+    }
+
+    return window;
+}
+
+
+void AlwaysOnTop::StepWindowTransparency(HWND window, int delta)
+{
+    HWND targetWindow = ResolveTransparencyTargetWindow(window);
+    if (!targetWindow)
+    {
+        return;
+    }
+
+    int currentTransparency = Settings::maxTransparencyPercentage;
+    LONG exStyle = GetWindowLong(targetWindow, GWL_EXSTYLE);
+    if (exStyle & WS_EX_LAYERED)
+    {
+        BYTE alpha = 255;
+        if (GetLayeredWindowAttributes(targetWindow, nullptr, &alpha, nullptr))
+        {
+            currentTransparency = (alpha * 100) / 255;
+        }
+    }
+
+    int newTransparency = (std::max)(Settings::minTransparencyPercentage, 
+                                     (std::min)(Settings::maxTransparencyPercentage, currentTransparency + delta));
+
+    if (newTransparency != currentTransparency)
+    {
+        ApplyWindowAlpha(targetWindow, newTransparency);
+
+        if (AlwaysOnTopSettings::settings().enableSound)
+        {
+            m_sound.Play(delta > 0 ? Sound::Type::IncreaseOpacity : Sound::Type::DecreaseOpacity);
+        }
+
+        Logger::debug(L"Transparency adjusted to {}%", newTransparency);
+    }
+}
+
+void AlwaysOnTop::ApplyWindowAlpha(HWND window, int percentage)
+{
+    if (!window || !IsWindow(window))
+    {
+        return;
+    }
+    
+    percentage = (std::max)(Settings::minTransparencyPercentage, 
+                            (std::min)(Settings::maxTransparencyPercentage, percentage));
+
+    LONG exStyle = GetWindowLong(window, GWL_EXSTYLE);
+    bool isCurrentlyLayered = (exStyle & WS_EX_LAYERED) != 0;
+
+    // Cache original state on first transparency application
+    if (m_windowOriginalLayeredState.find(window) == m_windowOriginalLayeredState.end())
+    {
+        WindowLayeredState state;
+        state.hadLayeredStyle = isCurrentlyLayered;
+        
+        if (isCurrentlyLayered)
+        {
+            BYTE alpha = 255;
+            COLORREF colorKey = 0;
+            DWORD flags = 0;
+            if (GetLayeredWindowAttributes(window, &colorKey, &alpha, &flags))
+            {
+                state.originalAlpha = alpha;
+                state.usedColorKey = (flags & LWA_COLORKEY) != 0;
+                state.colorKey = colorKey;
+            }
+            else
+            {
+                Logger::warn(L"GetLayeredWindowAttributes failed for layered window, skipping");
+                return;
+            }
+        }
+        m_windowOriginalLayeredState[window] = state;
+    }
+
+    // Clear WS_EX_LAYERED first to ensure SetLayeredWindowAttributes works
+    if (isCurrentlyLayered)
+    {
+        SetWindowLong(window, GWL_EXSTYLE, exStyle & ~WS_EX_LAYERED);
+        SetWindowPos(window, nullptr, 0, 0, 0, 0, SWP_NOMOVE | SWP_NOSIZE | SWP_NOZORDER | SWP_FRAMECHANGED);
+        exStyle = GetWindowLong(window, GWL_EXSTYLE);
+    }
+
+    BYTE alphaValue = static_cast<BYTE>((255 * percentage) / 100);
+    SetWindowLong(window, GWL_EXSTYLE, exStyle | WS_EX_LAYERED);
+    SetLayeredWindowAttributes(window, 0, alphaValue, LWA_ALPHA);
+}
+
+void AlwaysOnTop::RestoreWindowAlpha(HWND window)
+{
+    if (!window || !IsWindow(window))
+    {
+        return;
+    }
+
+    LONG exStyle = GetWindowLong(window, GWL_EXSTYLE);
+    auto it = m_windowOriginalLayeredState.find(window);
+    
+    if (it != m_windowOriginalLayeredState.end())
+    {
+        const auto& originalState = it->second;
+        
+        if (originalState.hadLayeredStyle)
+        {
+            // Window originally had WS_EX_LAYERED - restore original attributes
+            // Clear and re-add to ensure clean state
+            if (exStyle & WS_EX_LAYERED)
+            {
+                SetWindowLong(window, GWL_EXSTYLE, exStyle & ~WS_EX_LAYERED);
+                exStyle = GetWindowLong(window, GWL_EXSTYLE);
+            }
+            SetWindowLong(window, GWL_EXSTYLE, exStyle | WS_EX_LAYERED);
+            
+            // Restore original alpha and/or color key
+            DWORD flags = LWA_ALPHA;
+            if (originalState.usedColorKey)
+            {
+                flags |= LWA_COLORKEY;
+            }
+            SetLayeredWindowAttributes(window, originalState.colorKey, originalState.originalAlpha, flags);
+            SetWindowPos(window, nullptr, 0, 0, 0, 0, SWP_NOMOVE | SWP_NOSIZE | SWP_NOZORDER | SWP_FRAMECHANGED);
+        }
+        else
+        {
+            // Window originally didn't have WS_EX_LAYERED - remove it completely
+            if (exStyle & WS_EX_LAYERED)
+            {
+                SetLayeredWindowAttributes(window, 0, 255, LWA_ALPHA);
+                SetWindowLong(window, GWL_EXSTYLE, exStyle & ~WS_EX_LAYERED);
+                SetWindowPos(window, nullptr, 0, 0, 0, 0, SWP_NOMOVE | SWP_NOSIZE | SWP_NOZORDER | SWP_FRAMECHANGED);
+            }
+        }
+        
+        m_windowOriginalLayeredState.erase(it);
+    }
+    else
+    {
+        // Fallback: no cached state, just remove layered style
+        if (exStyle & WS_EX_LAYERED)
+        {
+            SetLayeredWindowAttributes(window, 0, 255, LWA_ALPHA);
+            SetWindowLong(window, GWL_EXSTYLE, exStyle & ~WS_EX_LAYERED);
+        }
+    }
 }

src/modules/alwaysontop/AlwaysOnTop/AlwaysOnTop.h

@@ -10,6 +10,7 @@
 
 #include <common/hooks/WinHookEvent.h>
 #include <common/notifications/NotificationUtil.h>
+#include <common/utils/window.h>
 
 class AlwaysOnTop : public SettingsObserver
 {
@@ -38,6 +39,8 @@ private:
     enum class HotkeyId : int
     {
         Pin = 1,
+        IncreaseOpacity = 2,
+        DecreaseOpacity = 3,
     };
 
     static inline AlwaysOnTop* s_instance = nullptr;
@@ -48,8 +51,20 @@ private:
     HWND m_window{ nullptr };
     HINSTANCE m_hinstance;
     std::map<HWND, std::unique_ptr<WindowBorder>> m_topmostWindows{};
+    
+    // Store original window layered state for proper restoration
+    struct WindowLayeredState {
+        bool hadLayeredStyle = false;
+        BYTE originalAlpha = 255;
+        bool usedColorKey = false;
+        COLORREF colorKey = 0;
+    };
+    std::map<HWND, WindowLayeredState> m_windowOriginalLayeredState{};
+    
     HANDLE m_hPinEvent;
     HANDLE m_hTerminateEvent;
+    HANDLE m_hIncreaseOpacityEvent;
+    HANDLE m_hDecreaseOpacityEvent;
     DWORD m_mainThreadId;
     std::thread m_thread;
     const bool m_useCentralizedLLKH;
@@ -78,6 +93,12 @@ private:
     bool AssignBorder(HWND window);
     void RefreshBorders();
 
+    // Transparency methods
+    HWND ResolveTransparencyTargetWindow(HWND window);
+    void StepWindowTransparency(HWND window, int delta);
+    void ApplyWindowAlpha(HWND window, int percentage);
+    void RestoreWindowAlpha(HWND window);
+
     virtual void SettingsUpdate(SettingId type) override;
 
     static void CALLBACK WinHookProc(HWINEVENTHOOK winEventHook,

src/modules/alwaysontop/AlwaysOnTop/Settings.h

@@ -15,6 +15,9 @@ class SettingsObserver;
 struct Settings
 {
     PowerToysSettings::HotkeyObject hotkey = PowerToysSettings::HotkeyObject::from_settings(true, true, false, false, 84); // win + ctrl + T
+    static constexpr int minTransparencyPercentage = 20; // minimum transparency (can't go below 20%)
+    static constexpr int maxTransparencyPercentage = 100; // maximum (fully opaque)
+    static constexpr int transparencyStep = 10; // step size for +/- adjustment
     bool enableFrame = true;
     bool enableSound = true;
     bool roundCornersEnabled = true;

src/modules/alwaysontop/AlwaysOnTop/Sound.h

@@ -2,7 +2,6 @@
 
 #include "pch.h"
 
-#include <atomic>
 #include <mmsystem.h> // sound
 
 class Sound
@@ -12,12 +11,10 @@ public:
     {
         On,
         Off,
+        IncreaseOpacity,
+        DecreaseOpacity,
     };
     
-    Sound()
-        : isPlaying(false)
-    {}
-
     void Play(Type type)
     {
         BOOL success = false;
@@ -29,6 +26,12 @@ public:
         case Type::Off:
             success = PlaySound(TEXT("Media\\Speech Sleep.wav"), NULL, SND_FILENAME | SND_ASYNC);
             break;
+        case Type::IncreaseOpacity:
+            success = PlaySound(TEXT("Media\\Windows Hardware Insert.wav"), NULL, SND_FILENAME | SND_ASYNC);
+            break;
+        case Type::DecreaseOpacity:
+            success = PlaySound(TEXT("Media\\Windows Hardware Remove.wav"), NULL, SND_FILENAME | SND_ASYNC);
+            break;
         default:
             break;
         }
@@ -38,7 +41,4 @@ public:
             Logger::error(L"Sound playing error");
         }
     }
-
-private:
-    std::atomic<bool> isPlaying;
 };

src/modules/alwaysontop/AlwaysOnTopModuleInterface/dllmain.cpp

@@ -105,17 +105,28 @@ public:
         }
     }
 
-    virtual bool on_hotkey(size_t /*hotkeyId*/) override
+    virtual bool on_hotkey(size_t hotkeyId) override
     {
         if (m_enabled)
         {
-            Logger::trace(L"AlwaysOnTop hotkey pressed");
+            Logger::trace(L"AlwaysOnTop hotkey pressed, id={}", hotkeyId);
             if (!is_process_running())
             {
                 Enable();
             }
 
-            SetEvent(m_hPinEvent);
+            if (hotkeyId == 0)
+            {
+                SetEvent(m_hPinEvent);
+            }
+            else if (hotkeyId == 1)
+            {
+                SetEvent(m_hIncreaseOpacityEvent);
+            }
+            else if (hotkeyId == 2)
+            {
+                SetEvent(m_hDecreaseOpacityEvent);
+            }
 
             return true;
         }
@@ -125,19 +136,48 @@ public:
 
     virtual size_t get_hotkeys(Hotkey* hotkeys, size_t buffer_size) override
     {
+        size_t count = 0;
+        
+        // Hotkey 0: Pin/Unpin (e.g., Win+Ctrl+T)
         if (m_hotkey.key)
         {
-            if (hotkeys && buffer_size >= 1)
+            if (hotkeys && buffer_size > count)
             {
-                hotkeys[0] = m_hotkey;
+                hotkeys[count] = m_hotkey;
+                Logger::trace(L"AlwaysOnTop hotkey[0]: win={}, ctrl={}, shift={}, alt={}, key={}", 
+                    m_hotkey.win, m_hotkey.ctrl, m_hotkey.shift, m_hotkey.alt, m_hotkey.key);
             }
+            count++;
+        }
 
-            return 1;
-        }
-        else
+        // Hotkey 1: Increase opacity (same modifiers + VK_OEM_PLUS '=')
+        if (m_hotkey.key)
         {
-            return 0;
+            if (hotkeys && buffer_size > count)
+            {
+                hotkeys[count] = m_hotkey;
+                hotkeys[count].key = VK_OEM_PLUS; // '=' key
+                Logger::trace(L"AlwaysOnTop hotkey[1] (increase opacity): win={}, ctrl={}, shift={}, alt={}, key={}", 
+                    hotkeys[count].win, hotkeys[count].ctrl, hotkeys[count].shift, hotkeys[count].alt, hotkeys[count].key);
+            }
+            count++;
         }
+
+        // Hotkey 2: Decrease opacity (same modifiers + VK_OEM_MINUS '-')
+        if (m_hotkey.key)
+        {
+            if (hotkeys && buffer_size > count)
+            {
+                hotkeys[count] = m_hotkey;
+                hotkeys[count].key = VK_OEM_MINUS; // '-' key
+                Logger::trace(L"AlwaysOnTop hotkey[2] (decrease opacity): win={}, ctrl={}, shift={}, alt={}, key={}", 
+                    hotkeys[count].win, hotkeys[count].ctrl, hotkeys[count].shift, hotkeys[count].alt, hotkeys[count].key);
+            }
+            count++;
+        }
+
+        Logger::trace(L"AlwaysOnTop get_hotkeys returning count={}", count);
+        return count;
     }
 
     // Enable the powertoy
@@ -175,6 +215,8 @@ public:
         app_key = NonLocalizable::ModuleKey;
         m_hPinEvent = CreateDefaultEvent(CommonSharedConstants::ALWAYS_ON_TOP_PIN_EVENT);
         m_hTerminateEvent = CreateDefaultEvent(CommonSharedConstants::ALWAYS_ON_TOP_TERMINATE_EVENT);
+        m_hIncreaseOpacityEvent = CreateDefaultEvent(CommonSharedConstants::ALWAYS_ON_TOP_INCREASE_OPACITY_EVENT);
+        m_hDecreaseOpacityEvent = CreateDefaultEvent(CommonSharedConstants::ALWAYS_ON_TOP_DECREASE_OPACITY_EVENT);
         init_settings();
     }
 
@@ -292,6 +334,8 @@ private:
     // Handle to event used to pin/unpin windows
     HANDLE m_hPinEvent;
     HANDLE m_hTerminateEvent;
+    HANDLE m_hIncreaseOpacityEvent;
+    HANDLE m_hDecreaseOpacityEvent;
 };
 
 extern "C" __declspec(dllexport) PowertoyModuleIface* __cdecl powertoy_create()

src/modules/cmdpal/CommandPalette.slnf

@@ -15,6 +15,7 @@
       "src\\modules\\cmdpal\\Microsoft.CmdPal.UI.ViewModels\\Microsoft.CmdPal.UI.ViewModels.csproj",
       "src\\modules\\cmdpal\\Microsoft.CmdPal.UI\\Microsoft.CmdPal.UI.csproj",
       "src\\modules\\cmdpal\\Microsoft.Terminal.UI\\Microsoft.Terminal.UI.vcxproj",
+      "src\\modules\\cmdpal\\Tests\\Microsoft.CmdPal.Core.Common.UnitTests\\Microsoft.CmdPal.Core.Common.UnitTests.csproj",
       "src\\modules\\cmdpal\\Tests\\Microsoft.CmdPal.Ext.Apps.UnitTests\\Microsoft.CmdPal.Ext.Apps.UnitTests.csproj",
       "src\\modules\\cmdpal\\Tests\\Microsoft.CmdPal.Ext.Bookmarks.UnitTests\\Microsoft.CmdPal.Ext.Bookmarks.UnitTests.csproj",
       "src\\modules\\cmdpal\\Tests\\Microsoft.CmdPal.Ext.Calc.UnitTests\\Microsoft.CmdPal.Ext.Calc.UnitTests.csproj",
@@ -29,6 +30,7 @@
       "src\\modules\\cmdpal\\Tests\\Microsoft.CmdPal.Ext.WindowWalker.UnitTests\\Microsoft.CmdPal.Ext.WindowWalker.UnitTests.csproj",
       "src\\modules\\cmdpal\\Tests\\Microsoft.CmdPal.UI.ViewModels.UnitTests\\Microsoft.CmdPal.UI.ViewModels.UnitTests.csproj",
       "src\\modules\\cmdpal\\Tests\\Microsoft.CmdPal.UITests\\Microsoft.CmdPal.UITests.csproj",
+      "src\\modules\\cmdpal\\Tests\\Microsoft.CommandPalette.Extensions.Toolkit.UnitTests\\Microsoft.CommandPalette.Extensions.Toolkit.UnitTests.csproj",
       "src\\modules\\cmdpal\\ext\\Microsoft.CmdPal.Ext.Apps\\Microsoft.CmdPal.Ext.Apps.csproj",
       "src\\modules\\cmdpal\\ext\\Microsoft.CmdPal.Ext.Bookmark\\Microsoft.CmdPal.Ext.Bookmarks.csproj",
       "src\\modules\\cmdpal\\ext\\Microsoft.CmdPal.Ext.Calc\\Microsoft.CmdPal.Ext.Calc.csproj",

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Microsoft.CmdPal.Core.Common.csproj

@@ -9,4 +9,18 @@
     <PackageReference Include="Microsoft.Extensions.Hosting" />
   </ItemGroup>
 
+  <ItemGroup>
+    <Compile Update="Properties\Resources.Designer.cs">
+      <DesignTime>True</DesignTime>
+      <AutoGen>True</AutoGen>
+      <DependentUpon>Resources.resx</DependentUpon>
+    </Compile>
+  </ItemGroup>
+
+  <ItemGroup>
+    <EmbeddedResource Update="Properties\Resources.resx">
+      <Generator>ResXFileCodeGenerator</Generator>
+    </EmbeddedResource>
+  </ItemGroup>
+
 </Project>

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Properties/Resources.Designer.cs

@@ -0,0 +1,76 @@
+//------------------------------------------------------------------------------
+// <auto-generated>
+//     This code was generated by a tool.
+//     Runtime Version:4.0.30319.42000
+//
+//     Changes to this file may cause incorrect behavior and will be lost if
+//     the code is regenerated.
+// </auto-generated>
+//------------------------------------------------------------------------------
+
+namespace Microsoft.CmdPal.Core.Common.Properties {
+    using System;
+    
+    
+    /// <summary>
+    ///   A strongly-typed resource class, for looking up localized strings, etc.
+    /// </summary>
+    // This class was auto-generated by the StronglyTypedResourceBuilder
+    // class via a tool like ResGen or Visual Studio.
+    // To add or remove a member, edit your .ResX file then rerun ResGen
+    // with the /str option, or rebuild your VS project.
+    [global::System.CodeDom.Compiler.GeneratedCodeAttribute("System.Resources.Tools.StronglyTypedResourceBuilder", "18.0.0.0")]
+    [global::System.Diagnostics.DebuggerNonUserCodeAttribute()]
+    [global::System.Runtime.CompilerServices.CompilerGeneratedAttribute()]
+    internal class Resources {
+        
+        private static global::System.Resources.ResourceManager resourceMan;
+        
+        private static global::System.Globalization.CultureInfo resourceCulture;
+        
+        [global::System.Diagnostics.CodeAnalysis.SuppressMessageAttribute("Microsoft.Performance", "CA1811:AvoidUncalledPrivateCode")]
+        internal Resources() {
+        }
+        
+        /// <summary>
+        ///   Returns the cached ResourceManager instance used by this class.
+        /// </summary>
+        [global::System.ComponentModel.EditorBrowsableAttribute(global::System.ComponentModel.EditorBrowsableState.Advanced)]
+        internal static global::System.Resources.ResourceManager ResourceManager {
+            get {
+                if (object.ReferenceEquals(resourceMan, null)) {
+                    global::System.Resources.ResourceManager temp = new global::System.Resources.ResourceManager("Microsoft.CmdPal.Core.Common.Properties.Resources", typeof(Resources).Assembly);
+                    resourceMan = temp;
+                }
+                return resourceMan;
+            }
+        }
+        
+        /// <summary>
+        ///   Overrides the current thread's CurrentUICulture property for all
+        ///   resource lookups using this strongly typed resource class.
+        /// </summary>
+        [global::System.ComponentModel.EditorBrowsableAttribute(global::System.ComponentModel.EditorBrowsableState.Advanced)]
+        internal static global::System.Globalization.CultureInfo Culture {
+            get {
+                return resourceCulture;
+            }
+            set {
+                resourceCulture = value;
+            }
+        }
+        
+        /// <summary>
+        ///   Looks up a localized string similar to This is an error report generated by Windows Command Palette.
+        ///If you are seeing this, it means something went a little sideways in the app.
+        ///You can help us fix it by filing a report at https://aka.ms/powerToysReportBug.
+        ///
+        ///(While you’re at it, give the details below a quick skim — just to make sure there’s nothing personal you’d prefer not to share. It’s rare, but sometimes little surprises sneak in.).
+        /// </summary>
+        internal static string ErrorReport_Global_Preamble {
+            get {
+                return ResourceManager.GetString("ErrorReport_Global_Preamble", resourceCulture);
+            }
+        }
+    }
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Properties/Resources.resx

@@ -0,0 +1,127 @@
+<?xml version="1.0" encoding="utf-8"?>
+<root>
+  <!-- 
+    Microsoft ResX Schema 
+    
+    Version 2.0
+    
+    The primary goals of this format is to allow a simple XML format 
+    that is mostly human readable. The generation and parsing of the 
+    various data types are done through the TypeConverter classes 
+    associated with the data types.
+    
+    Example:
+    
+    ... ado.net/XML headers & schema ...
+    <resheader name="resmimetype">text/microsoft-resx</resheader>
+    <resheader name="version">2.0</resheader>
+    <resheader name="reader">System.Resources.ResXResourceReader, System.Windows.Forms, ...</resheader>
+    <resheader name="writer">System.Resources.ResXResourceWriter, System.Windows.Forms, ...</resheader>
+    <data name="Name1"><value>this is my long string</value><comment>this is a comment</comment></data>
+    <data name="Color1" type="System.Drawing.Color, System.Drawing">Blue</data>
+    <data name="Bitmap1" mimetype="application/x-microsoft.net.object.binary.base64">
+        <value>[base64 mime encoded serialized .NET Framework object]</value>
+    </data>
+    <data name="Icon1" type="System.Drawing.Icon, System.Drawing" mimetype="application/x-microsoft.net.object.bytearray.base64">
+        <value>[base64 mime encoded string representing a byte array form of the .NET Framework object]</value>
+        <comment>This is a comment</comment>
+    </data>
+                
+    There are any number of "resheader" rows that contain simple 
+    name/value pairs.
+    
+    Each data row contains a name, and value. The row also contains a 
+    type or mimetype. Type corresponds to a .NET class that support 
+    text/value conversion through the TypeConverter architecture. 
+    Classes that don't support this are serialized and stored with the 
+    mimetype set.
+    
+    The mimetype is used for serialized objects, and tells the 
+    ResXResourceReader how to depersist the object. This is currently not 
+    extensible. For a given mimetype the value must be set accordingly:
+    
+    Note - application/x-microsoft.net.object.binary.base64 is the format 
+    that the ResXResourceWriter will generate, however the reader can 
+    read any of the formats listed below.
+    
+    mimetype: application/x-microsoft.net.object.binary.base64
+    value   : The object must be serialized with 
+            : System.Runtime.Serialization.Formatters.Binary.BinaryFormatter
+            : and then encoded with base64 encoding.
+    
+    mimetype: application/x-microsoft.net.object.soap.base64
+    value   : The object must be serialized with 
+            : System.Runtime.Serialization.Formatters.Soap.SoapFormatter
+            : and then encoded with base64 encoding.
+
+    mimetype: application/x-microsoft.net.object.bytearray.base64
+    value   : The object must be serialized into a byte array 
+            : using a System.ComponentModel.TypeConverter
+            : and then encoded with base64 encoding.
+    -->
+  <xsd:schema id="root" xmlns="" xmlns:xsd="http://www.w3.org/2001/XMLSchema" xmlns:msdata="urn:schemas-microsoft-com:xml-msdata">
+    <xsd:import namespace="http://www.w3.org/XML/1998/namespace" />
+    <xsd:element name="root" msdata:IsDataSet="true">
+      <xsd:complexType>
+        <xsd:choice maxOccurs="unbounded">
+          <xsd:element name="metadata">
+            <xsd:complexType>
+              <xsd:sequence>
+                <xsd:element name="value" type="xsd:string" minOccurs="0" />
+              </xsd:sequence>
+              <xsd:attribute name="name" use="required" type="xsd:string" />
+              <xsd:attribute name="type" type="xsd:string" />
+              <xsd:attribute name="mimetype" type="xsd:string" />
+              <xsd:attribute ref="xml:space" />
+            </xsd:complexType>
+          </xsd:element>
+          <xsd:element name="assembly">
+            <xsd:complexType>
+              <xsd:attribute name="alias" type="xsd:string" />
+              <xsd:attribute name="name" type="xsd:string" />
+            </xsd:complexType>
+          </xsd:element>
+          <xsd:element name="data">
+            <xsd:complexType>
+              <xsd:sequence>
+                <xsd:element name="value" type="xsd:string" minOccurs="0" msdata:Ordinal="1" />
+                <xsd:element name="comment" type="xsd:string" minOccurs="0" msdata:Ordinal="2" />
+              </xsd:sequence>
+              <xsd:attribute name="name" type="xsd:string" use="required" msdata:Ordinal="1" />
+              <xsd:attribute name="type" type="xsd:string" msdata:Ordinal="3" />
+              <xsd:attribute name="mimetype" type="xsd:string" msdata:Ordinal="4" />
+              <xsd:attribute ref="xml:space" />
+            </xsd:complexType>
+          </xsd:element>
+          <xsd:element name="resheader">
+            <xsd:complexType>
+              <xsd:sequence>
+                <xsd:element name="value" type="xsd:string" minOccurs="0" msdata:Ordinal="1" />
+              </xsd:sequence>
+              <xsd:attribute name="name" type="xsd:string" use="required" />
+            </xsd:complexType>
+          </xsd:element>
+        </xsd:choice>
+      </xsd:complexType>
+    </xsd:element>
+  </xsd:schema>
+  <resheader name="resmimetype">
+    <value>text/microsoft-resx</value>
+  </resheader>
+  <resheader name="version">
+    <value>2.0</value>
+  </resheader>
+  <resheader name="reader">
+    <value>System.Resources.ResXResourceReader, System.Windows.Forms, Version=4.0.0.0, Culture=neutral, PublicKeyToken=b77a5c561934e089</value>
+  </resheader>
+  <resheader name="writer">
+    <value>System.Resources.ResXResourceWriter, System.Windows.Forms, Version=4.0.0.0, Culture=neutral, PublicKeyToken=b77a5c561934e089</value>
+  </resheader>
+  <data name="ErrorReport_Global_Preamble" xml:space="preserve">
+    <value>This is an error report generated by Windows Command Palette.
+If you are seeing this, it means something went a little sideways in the app.
+You can help us fix it by filing a report at https://aka.ms/powerToysReportBug.
+
+(While you’re at it, give the details below a quick skim — just to make sure there’s nothing personal you’d prefer not to share. It’s rare, but sometimes little surprises sneak in.)</value>
+  </data>
+</root>

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Reports/ErrorReportBuilder.cs

@@ -0,0 +1,118 @@
+// 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.Globalization;
+using System.Runtime.InteropServices;
+using System.Security.Principal;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+using Windows.ApplicationModel;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Reports;
+
+public sealed class ErrorReportBuilder : IErrorReportBuilder
+{
+    private readonly ErrorReportSanitizer _sanitizer = new();
+
+    private static string Preamble => Properties.Resources.ErrorReport_Global_Preamble;
+
+    public string BuildReport(Exception exception, string context, bool redactPii = true)
+    {
+        ArgumentNullException.ThrowIfNull(exception);
+
+        var exceptionMessage = CoalesceExceptionMessage(exception);
+        var sanitizedMessage = redactPii ? _sanitizer.Sanitize(exceptionMessage) : exceptionMessage;
+        var sanitizedFormattedException = redactPii ? _sanitizer.Sanitize(exception.ToString()) : exception.ToString();
+
+        // Note:
+        // - do not localize technical part of the report, we need to ensure it can be read by developers
+        // - keep timestamp format should be consistent with the log (makes it easier to search)
+        var technicalContent =
+               $"""
+                ============================================================
+                Summary:
+                  Message:               {sanitizedMessage}
+                  Type:                  {exception.GetType().FullName}
+                  Source:                {exception.Source ?? "N/A"}
+                  Time:                  {DateTime.Now:yyyy-MM-dd HH:mm:ss.fffffff}
+                  HRESULT:               0x{exception.HResult:X8} ({exception.HResult})
+                  Context:               {context ?? "N/A"}
+
+                Application:
+                  App version:           {GetAppVersionSafe()}
+                  Is elevated:           {GetElevationStatus()}
+
+                Environment:
+                  OS version:            {RuntimeInformation.OSDescription}
+                  OS architecture:       {RuntimeInformation.OSArchitecture}
+                  Runtime identifier:    {RuntimeInformation.RuntimeIdentifier}
+                  Framework:             {RuntimeInformation.FrameworkDescription}
+                  Process architecture:  {RuntimeInformation.ProcessArchitecture}
+                  Culture:               {CultureInfo.CurrentCulture.Name}
+                  UI culture:            {CultureInfo.CurrentUICulture.Name}
+
+                Stack Trace:
+                {exception.StackTrace}
+
+                ------------------ Full Exception Details ------------------
+                {sanitizedFormattedException}
+
+                ============================================================
+                """;
+
+        return $"""
+                {Preamble}
+                {technicalContent}
+                """;
+    }
+
+    private static string GetElevationStatus()
+    {
+        // Note: do not localize technical part of the report, we need to ensure it can be read by developers
+        try
+        {
+            var isElevated = new WindowsPrincipal(WindowsIdentity.GetCurrent()).IsInRole(WindowsBuiltInRole.Administrator);
+            return isElevated ? "yes" : "no";
+        }
+        catch (Exception)
+        {
+            return "Failed to determine elevation status";
+        }
+    }
+
+    private static string GetAppVersionSafe()
+    {
+        // Note: do not localize technical part of the report, we need to ensure it can be read by developers
+        try
+        {
+            var version = Package.Current.Id.Version;
+            return $"{version.Major}.{version.Minor}.{version.Build}.{version.Revision}";
+        }
+        catch (Exception)
+        {
+            return "Failed to retrieve app version";
+        }
+    }
+
+    private static string CoalesceExceptionMessage(Exception exception)
+    {
+        // let's try to get a message from the exception or inferred it from the HRESULT
+        // to show at least something
+        var message = exception.Message;
+        if (string.IsNullOrWhiteSpace(message))
+        {
+            var temp = Marshal.GetExceptionForHR(exception.HResult)?.Message;
+            if (!string.IsNullOrWhiteSpace(temp))
+            {
+                message = temp + $" (inferred from HRESULT 0x{exception.HResult:X8})";
+            }
+        }
+
+        if (string.IsNullOrWhiteSpace(message))
+        {
+            message = "No message available";
+        }
+
+        return message;
+    }
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Reports/IErrorReportBuilder.cs

@@ -0,0 +1,33 @@
+// 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.Core.Common.Services.Reports;
+
+/// <summary>
+/// Defines a contract for creating human-readable error reports from exceptions,
+/// suitable for logs, telemetry, or user-facing diagnostics.
+/// </summary>
+/// <remarks>
+/// Implementations should ensure reports are consistent and optionally redact
+/// personally identifiable or sensitive information when requested.
+/// </remarks>
+public interface IErrorReportBuilder
+{
+    /// <summary>
+    /// Builds a formatted error report for the specified <paramref name="exception"/> and <paramref name="context"/>.
+    /// </summary>
+    /// <param name="exception">The exception that triggered the error report.</param>
+    /// <param name="context">
+    /// A short, human-readable description of where or what was being executed when the error occurred
+    /// (e.g., the operation name, component, or scenario).
+    /// </param>
+    /// <param name="redactPii">
+    /// When true, attempts to remove or obfuscate personally identifiable or sensitive information
+    /// (such as file paths, emails, machine/usernames, tokens). Defaults to true.
+    /// </param>
+    /// <returns>
+    /// A formatted string containing the error report, suitable for logging or telemetry submission.
+    /// </returns>
+    string BuildReport(Exception exception, string context, bool redactPii = true);
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/Abstraction/ITextSanitizer.cs

@@ -0,0 +1,61 @@
+// 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.Core.Common.Services.Sanitizer.Abstraction;
+
+/// <summary>
+/// Defines a service that sanitizes text by applying a set of configurable, regex-based rules.
+/// Typical use cases include masking secrets, removing PII, or normalizing logs.
+/// </summary>
+/// <remarks>
+/// - Rules are applied in their registered order; rule ordering may affect the final output.
+/// - Each rule should have a unique <c>description</c> that acts as its identifier.
+/// </remarks>
+/// <seealso cref="SanitizationRule"/>
+public interface ITextSanitizer
+{
+    /// <summary>
+    /// Sanitizes the specified input by applying all registered rules in order.
+    /// </summary>
+    /// <param name="input">The input text to sanitize. Implementations should handle <see langword="null"/> safely.</param>
+    /// <returns>The sanitized text after all rules are applied.</returns>
+    string Sanitize(string? input);
+
+    /// <summary>
+    /// Adds a sanitization rule using a .NET regular expression pattern and a replacement string.
+    /// </summary>
+    /// <param name="pattern">A .NET regular expression pattern used to match text to sanitize.</param>
+    /// <param name="replacement">
+    /// The replacement text used by <c>Regex.Replace</c>. Supports standard regex replacement tokens,
+    /// including numbered groups (<c>$1</c>) and named groups (<c>${name}</c>).
+    /// </param>
+    /// <param name="description">
+    /// A human-readable, unique identifier for the rule. Used to list, test, and remove the rule.
+    /// </param>
+    /// <remarks>
+    /// Implementations typically validate <paramref name="pattern"/> is a valid regex and may reject duplicate <paramref name="description"/> values.
+    /// </remarks>
+    void AddRule(string pattern, string replacement, string description = "");
+
+    /// <summary>
+    /// Removes a previously added rule identified by its <paramref name="description"/>.
+    /// </summary>
+    /// <param name="description">The unique description of the rule to remove.</param>
+    void RemoveRule(string description);
+
+    /// <summary>
+    /// Gets a read-only snapshot of the currently registered sanitization rules in application order.
+    /// </summary>
+    /// <returns>A read-only list of <see cref="SanitizationRule"/> items.</returns>
+    IReadOnlyList<SanitizationRule> GetRules();
+
+    /// <summary>
+    /// Tests a single rule, identified by <paramref name="ruleDescription"/>, against the provided <paramref name="input"/>,
+    /// without applying other rules.
+    /// </summary>
+    /// <param name="input">The input text to test.</param>
+    /// <param name="ruleDescription">The description (identifier) of the rule to test.</param>
+    /// <returns>The result of applying only the specified rule to the input.</returns>
+    string TestRule(string input, string ruleDescription);
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/Abstraction/SanitizationRule.cs

@@ -0,0 +1,36 @@
+// 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.Text.RegularExpressions;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+public readonly record struct SanitizationRule
+{
+    public SanitizationRule(Regex regex, string replacement, string description = "")
+    {
+        Regex = regex;
+        Replacement = replacement;
+        Evaluator = null;
+        Description = description;
+    }
+
+    public SanitizationRule(Regex regex, MatchEvaluator evaluator, string description = "")
+    {
+        Regex = regex;
+        Evaluator = evaluator;
+        Replacement = null;
+        Description = description;
+    }
+
+    public Regex Regex { get; }
+
+    public string? Replacement { get; }
+
+    public MatchEvaluator? Evaluator { get; }
+
+    public string Description { get; }
+
+    public override string ToString() => $"{Description}: {Regex} -> {Replacement ?? "<evaluator>"}";
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/ConnectionStringRuleProvider.cs

@@ -0,0 +1,20 @@
+// 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.Text.RegularExpressions;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+
+internal sealed partial class ConnectionStringRuleProvider : ISanitizationRuleProvider
+{
+    [GeneratedRegex(@"(Server|Data Source|Initial Catalog|Database|User ID|Username|Password|Pwd|Uid)\s*=\s*(?:""[^""]*""|'[^']*'|[^;,\s]+)",
+        SanitizerDefaults.DefaultOptions, SanitizerDefaults.DefaultMatchTimeoutMs)]
+    private static partial Regex ConnectionParamRx();
+
+    public IEnumerable<SanitizationRule> GetRules()
+    {
+        yield return new(ConnectionParamRx(), "$1=[REDACTED]", "Connection string parameters");
+    }
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/EnvironmentPropertiesRuleProvider.cs

@@ -0,0 +1,32 @@
+// 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.Text.RegularExpressions;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+
+internal sealed class EnvironmentPropertiesRuleProvider : ISanitizationRuleProvider
+{
+    public IEnumerable<SanitizationRule> GetRules()
+    {
+        List<SanitizationRule> rules = [];
+
+        var machine = Environment.MachineName;
+        if (!string.IsNullOrWhiteSpace(machine))
+        {
+            var rx = new Regex(@"\b" + Regex.Escape(machine) + @"\b", SanitizerDefaults.DefaultOptions, TimeSpan.FromMilliseconds(SanitizerDefaults.DefaultMatchTimeoutMs));
+            rules.Add(new(rx, "[MACHINE_NAME_REDACTED]", "Machine name"));
+        }
+
+        var domain = Environment.UserDomainName;
+        if (!string.IsNullOrWhiteSpace(domain))
+        {
+            var rx = new Regex(@"\b" + Regex.Escape(domain) + @"\b", SanitizerDefaults.DefaultOptions, TimeSpan.FromMilliseconds(SanitizerDefaults.DefaultMatchTimeoutMs));
+            rules.Add(new(rx, "[USER_DOMAIN_NAME_REDACTED]", "User domain name"));
+        }
+
+        return rules;
+    }
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/ErrorReportSanitizer.cs

@@ -0,0 +1,85 @@
+// Copyright (c) Microsoft Corporation
+// The Microsoft Corporation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+
+/// <summary>
+/// Specific sanitizer used for error report content. Builds on top of the generic TextSanitizer.
+/// </summary>
+public sealed class ErrorReportSanitizer
+{
+    private readonly TextSanitizer _sanitizer = new(BuildProviders(), onGuardrailTriggered: OnGuardrailTriggered);
+
+    private static void OnGuardrailTriggered(GuardrailEventArgs eventArgs)
+    {
+        var msg = $"Sanitization guardrail triggered for rule '{eventArgs.RuleDescription}': original length={eventArgs.OriginalLength}, result length={eventArgs.ResultLength}, ratio={eventArgs.Ratio:F2}, threshold={eventArgs.Threshold:F2}";
+        CoreLogger.LogDebug(msg);
+    }
+
+    private static IEnumerable<ISanitizationRuleProvider> BuildProviders()
+    {
+        // Order matters
+        return
+        [
+            new PiiRuleProvider(),
+            new UrlRuleProvider(),
+            new NetworkRuleProvider(),
+            new TokenRuleProvider(),
+            new ConnectionStringRuleProvider(),
+            new SecretKeyValueRulesProvider(),
+            new EnvironmentPropertiesRuleProvider(),
+            new FilenameMaskRuleProvider(),
+            new ProfilePathAndUsernameRuleProvider()
+        ];
+    }
+
+    public string Sanitize(string? input) => _sanitizer.Sanitize(input);
+
+    public string SanitizeException(Exception? exception)
+    {
+        if (exception is null)
+        {
+            return string.Empty;
+        }
+
+        var fullMessage = GetFullExceptionMessage(exception);
+        return Sanitize(fullMessage);
+    }
+
+    private static string GetFullExceptionMessage(Exception exception)
+    {
+        List<string> messages = [];
+        var current = exception;
+        var depth = 0;
+
+        // Prevent infinite loops on pathological InnerException graphs
+        while (current is not null && depth < 10)
+        {
+            messages.Add($"{current.GetType().Name}: {current.Message}");
+
+            if (!string.IsNullOrEmpty(current.StackTrace))
+            {
+                messages.Add($"Stack Trace: {current.StackTrace}");
+            }
+
+            current = current.InnerException;
+            depth++;
+        }
+
+        return string.Join(Environment.NewLine, messages);
+    }
+
+    public void AddRule(string pattern, string replacement, string description = "")
+        => _sanitizer.AddRule(pattern, replacement, description);
+
+    public void RemoveRule(string description)
+        => _sanitizer.RemoveRule(description);
+
+    public IReadOnlyList<SanitizationRule> GetRules() => _sanitizer.GetRules();
+
+    public string TestRule(string input, string ruleDescription)
+        => _sanitizer.TestRule(input, ruleDescription);
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/FilenameMaskRuleProvider.cs

@@ -0,0 +1,109 @@
+// Copyright (c) Microsoft Corporation
+// The Microsoft Corporation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+using System.Collections.Frozen;
+using System.Text.RegularExpressions;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+
+internal sealed class FilenameMaskRuleProvider : ISanitizationRuleProvider
+{
+    private static readonly FrozenSet<string> CommonFileStemExclusions = new[]
+    {
+        "settings",
+        "config",
+        "configuration",
+        "appsettings",
+        "options",
+        "prefs",
+        "preferences",
+        "squirrel",
+        "app",
+        "system",
+        "env",
+        "environment",
+        "manifest",
+    }.ToFrozenSet(StringComparer.OrdinalIgnoreCase);
+
+    public IEnumerable<SanitizationRule> GetRules()
+    {
+        const string pattern = """
+        (?<full>
+            (?: [A-Za-z]: )? (?: [\\/][^\\/:*?""<>|\s]+ )+       # drive-rooted or UNC-like
+          |     [^\\/:*?""<>|\s]+ (?: [\\/][^\\/:*?""<>|\s]+ )+  # relative with at least one sep
+        )
+        """;
+
+        var rx = new Regex(pattern, SanitizerDefaults.DefaultOptions | RegexOptions.IgnorePatternWhitespace, TimeSpan.FromMilliseconds(SanitizerDefaults.DefaultMatchTimeoutMs));
+        yield return new SanitizationRule(rx, MatchEvaluator, "Mask filename in any path");
+        yield break;
+
+        static string MatchEvaluator(Match m)
+        {
+            var full = m.Groups["full"].Value;
+
+            var lastSep = Math.Max(full.LastIndexOf('\\'), full.LastIndexOf('/'));
+            if (lastSep < 0 || lastSep == full.Length - 1)
+            {
+                return full;
+            }
+
+            var dir = full[..(lastSep + 1)];
+            var file = full[(lastSep + 1)..];
+
+            var dot = file.LastIndexOf('.');
+            var looksLikeFile = (dot > 0 && dot < file.Length - 1) || (file.StartsWith('.') && file.Length > 1);
+
+            if (!looksLikeFile)
+            {
+                return full;
+            }
+
+            string stem, ext;
+            if (dot > 0 && dot < file.Length - 1)
+            {
+                stem = file[..dot];
+                ext = file[dot..];
+            }
+            else
+            {
+                stem = file;
+                ext = string.Empty;
+            }
+
+            if (!ShouldMaskFileName(stem))
+            {
+                return dir + file;
+            }
+
+            var masked = MaskStem(stem) + ext;
+            return dir + masked;
+        }
+    }
+
+    private static string NormalizeStem(string stem)
+    {
+        return stem.Replace("-", string.Empty, StringComparison.Ordinal)
+            .Replace("_", string.Empty, StringComparison.Ordinal)
+            .Replace(".", string.Empty, StringComparison.Ordinal);
+    }
+
+    private static bool ShouldMaskFileName(string stem)
+    {
+        return !CommonFileStemExclusions.Contains(NormalizeStem(stem));
+    }
+
+    private static string MaskStem(string stem)
+    {
+        if (string.IsNullOrEmpty(stem))
+        {
+            return stem;
+        }
+
+        var keep = Math.Min(2, stem.Length);
+        var maskedCount = Math.Max(1, stem.Length - keep);
+        return stem[..keep] + new string('*', maskedCount);
+    }
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/GuardrailEventArgs.cs

@@ -0,0 +1,14 @@
+// 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.Core.Common.Services.Sanitizer;
+
+public record GuardrailEventArgs(
+    string RuleDescription,
+    int OriginalLength,
+    int ResultLength,
+    double Threshold)
+{
+    public double Ratio => OriginalLength > 0 ? (double)ResultLength / OriginalLength : 1.0;
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/ISanitizationRuleProvider.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.
+
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+
+internal interface ISanitizationRuleProvider
+{
+    IEnumerable<SanitizationRule> GetRules();
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/NetworkRuleProvider.cs

@@ -0,0 +1,84 @@
+// 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.Text.RegularExpressions;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+
+internal sealed partial class NetworkRuleProvider : ISanitizationRuleProvider
+{
+    public IEnumerable<SanitizationRule> GetRules()
+    {
+        yield return new(Ipv4Rx(), "[IP4_REDACTED]", "IP addresses");
+        yield return new(Ipv6BracketedRx(), "[IP6_REDACTED]", "IPv6 addresses (bracketed/with port)");
+        yield return new(Ipv6Rx(), "[IP6_REDACTED]", "IPv6 addresses");
+        yield return new(MacAddressRx(), "[MAC_ADDRESS_REDACTED]", "MAC addresses");
+    }
+
+    [GeneratedRegex(@"\b(?:(?:25[0-5]|2[0-4][0-9]|[01]?[0-9][0-9]?)\.){3}(?:25[0-5]|2[0-4][0-9]|[01]?[0-9][0-9]?)\b",
+        SanitizerDefaults.DefaultOptions, SanitizerDefaults.DefaultMatchTimeoutMs)]
+    private static partial Regex Ipv4Rx();
+
+    [GeneratedRegex(
+        """
+        (?ix)                                  # ignore case/whitespace
+              (?<![A-F0-9:])                        # left edge
+              (
+                (?:[A-F0-9]{1,4}:){7}[A-F0-9]{1,4}                | # 1:2:3:4:5:6:7:8
+                (?:[A-F0-9]{1,4}:){1,7}:                           | # 1:: 1:2:...:7::
+                (?:[A-F0-9]{1,4}:){1,6}:[A-F0-9]{1,4}             |
+                (?:[A-F0-9]{1,4}:){1,5}(?::[A-F0-9]{1,4}){1,2}    |
+                (?:[A-F0-9]{1,4}:){1,4}(?::[A-F0-9]{1,4}){1,3}    |
+                (?:[A-F0-9]{1,4}:){1,3}(?::[A-F0-9]{1,4}){1,4}    |
+                (?:[A-F0-9]{1,4}:){1,2}(?::[A-F0-9]{1,4}){1,5}    |
+                [A-F0-9]{1,4}:(?::[A-F0-9]{1,4}){1,6}             |
+                :(?::[A-F0-9]{1,4}){1,7}                          | # ::, ::1, etc.
+                (?:[A-F0-9]{1,4}:){6}\d{1,3}(?:\.\d{1,3}){3}      | # IPv4 tail
+                (?:[A-F0-9]{1,4}:){1,5}:(?:\d{1,3}\.){3}\d{1,3}   |
+                (?:[A-F0-9]{1,4}:){1,4}:(?:\d{1,3}\.){3}\d{1,3}   |
+                (?:[A-F0-9]{1,4}:){1,3}:(?:\d{1,3}\.){3}\d{1,3}   |
+                (?:[A-F0-9]{1,4}:){1,2}:(?:\d{1,3}\.){3}\d{1,3}   |
+                [A-F0-9]{1,4}:(?:\d{1,3}\.){3}\d{1,3}             |
+                :(?:\d{1,3}\.){3}\d{1,3}
+              )
+              (?:%\w+)?                               # optional zone id
+              (?![A-F0-9:])                           # right edge
+        """,
+        SanitizerDefaults.DefaultOptions | RegexOptions.IgnorePatternWhitespace, SanitizerDefaults.DefaultMatchTimeoutMs)]
+    private static partial Regex Ipv6Rx();
+
+    [GeneratedRegex(
+        """
+    (?ix)
+          \[
+            (
+              (?:[A-F0-9]{1,4}:){7}[A-F0-9]{1,4}              |
+              (?:[A-F0-9]{1,4}:){1,7}:                         |
+              (?:[A-F0-9]{1,4}:){1,6}:[A-F0-9]{1,4}           |
+              (?:[A-F0-9]{1,4}:){1,5}(?::[A-F0-9]{1,4}){1,2}  |
+              (?:[A-F0-9]{1,4}:){1,4}(?::[A-F0-9]{1,4}){1,3}  |
+              (?:[A-F0-9]{1,4}:){1,3}(?::[A-F0-9]{1,4}){1,4}  |
+              (?:[A-F0-9]{1,4}:){1,2}(?::[A-F0-9]{1,4}){1,5}  |
+              [A-F0-9]{1,4}:(?::[A-F0-9]{1,4}){1,6}           |
+              :(?::[A-F0-9]{1,4}){1,7}                        |
+              (?:[A-F0-9]{1,4}:){6}\d{1,3}(?:\.\d{1,3}){3}    |
+              (?:[A-F0-9]{1,4}:){1,5}:(?:\d{1,3}\.){3}\d{1,3} |
+              (?:[A-F0-9]{1,4}:){1,4}:(?:\d{1,3}\.){3}\d{1,3} |
+              (?:[A-F0-9]{1,4}:){1,3}:(?:\d{1,3}\.){3}\d{1,3} |
+              (?:[A-F0-9]{1,4}:){1,2}:(?:\d{1,3}\.){3}\d{1,3} |
+              [A-F0-9]{1,4}:(?:\d{1,3}\.){3}\d{1,3}           |
+              :(?:\d{1,3}\.){3}\d{1,3}
+            )
+            (?:%\w+)?                          # optional zone id
+          \]
+          (?: : (?<port>\d{1,5}) )?            # optional port
+    """,
+        SanitizerDefaults.DefaultOptions | RegexOptions.IgnorePatternWhitespace, SanitizerDefaults.DefaultMatchTimeoutMs)]
+    private static partial Regex Ipv6BracketedRx();
+
+    [GeneratedRegex(@"\b(?:[0-9A-Fa-f]{2}[:-]){5}(?:[0-9A-Fa-f]{2}|[0-9A-Fa-f]{1,2})\b",
+        SanitizerDefaults.DefaultOptions, SanitizerDefaults.DefaultMatchTimeoutMs)]
+    private static partial Regex MacAddressRx();
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/PiiRuleProvider.cs

@@ -0,0 +1,83 @@
+// 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.Text.RegularExpressions;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+
+internal sealed partial class PiiRuleProvider : ISanitizationRuleProvider
+{
+    public IEnumerable<SanitizationRule> GetRules()
+    {
+        yield return new(EmailRx(), "[EMAIL_REDACTED]", "Email addresses");
+        yield return new(SsnRx(), "[SSN_REDACTED]", "Social Security Numbers");
+        yield return new(CreditCardRx(), "[CARD_REDACTED]", "Credit card numbers");
+
+        // phone number regex is the most generic, so it goes last
+        // we can't make this too generic; otherwise we over-redact error codes, dates, etc.
+        yield return new(PhoneRx(), "[PHONE_REDACTED]", "Phone numbers");
+    }
+
+    [GeneratedRegex(@"\b[a-zA-Z0-9]([a-zA-Z0-9._%-]*[a-zA-Z0-9])?@[a-zA-Z0-9]([a-zA-Z0-9.-]*[a-zA-Z0-9])?\.[a-zA-Z]{2,}\b",
+        SanitizerDefaults.DefaultOptions, SanitizerDefaults.DefaultMatchTimeoutMs)]
+    private static partial Regex EmailRx();
+
+    [GeneratedRegex("""
+                    (?xi)
+                    # ---------- boundaries ----------
+                    (?<!\w)                          # not after a letter/digit/underscore
+                    (?<![A-Za-z0-9]-)                # avoid starting inside hyphenated tokens (GUID middles, etc.)
+
+                    # ---------- global do-not-match guards ----------
+                    (?!                              # ISO date (yyyy-mm-dd / yyyy.mm.dd / yyyy/mm/dd)
+                       (?:19|20)\d{2}[-./](?:0[1-9]|1[0-2])[-./](?:0[1-9]|[12]\d|3[01])\b
+                    )
+                    (?!                              # EU date (dd-mm-yyyy / dd.mm.yyyy / dd/mm/yyyy)
+                       (?:0[1-9]|[12]\d|3[01])[-./](?:0[1-9]|1[0-2])[-./](?:19|20)\d{2}\b
+                    )
+                    (?!                              # ISO datetime like 2025-08-24T14:32[:ss][Z|±hh:mm]
+                       (?:19|20)\d{2}-\d{2}-\d{2}[T\s]\d{2}:\d{2}(?::\d{2})?(?:Z|[+-]\d{2}:\d{2})?\b
+                    )
+                    (?!\b(?:\d{1,3}\.){3}\d{1,3}(?::\d{1,5})?\b)   # IPv4 with optional :port
+                    (?!\b[0-9a-f]{8}-(?:[0-9a-f]{4}-){3}[0-9a-f]{12}\b)  # GUID, lowercase
+                    (?!\b[0-9A-F]{8}-(?:[0-9A-F]{4}-){3}[0-9A-F]{12}\b)  # GUID, uppercase
+                    (?!\bv?\d+(?:\.\d+){2,}\b)       # semantic/file versions like 1.2.3 or 10.0.22631.3448
+                    (?!\b(?:[0-9A-F]{2}[:-]){5}[0-9A-F]{2}\b)       # MAC address
+
+                    # ---------- digit budget ----------
+                    (?=(?:\D*\d){7,15})              # 7–15 digits in total
+
+                    # ---------- number body ----------
+                    (?:
+                      # A with explicit country code, allow compact digits (E.164-ish) or grouped
+                      (?:\+|00)[1-9]\d{0,2}
+                      (?:
+                        [\p{Zs}.\-\/]*\d{6,14}
+                        |
+                        [\p{Zs}.\-\/]* (?:\(\d{1,4}\)|\d{1,4})
+                        (?:[\p{Zs}.\-\/]+(?:\(\d{2,4}\)|\d{2,4})){1,6}
+                      )
+                      |
+                      # B no country code => require separators between blocks (avoid plain big ints)
+                      (?:\(\d{1,4}\)|\d{1,4})
+                      (?:[\p{Zs}.\-\/]+(?:\(\d{2,4}\)|\d{2,4})){1,6}
+                    )
+
+                    # ---------- optional extension ----------
+                    (?:[\p{Zs}.\-,:;]* (?:ext\.?|x) [\p{Zs}]* (?<ext>\d{1,6}))?
+
+                    (?!-\w)                           # don't end just before '-letter'/'-digit'
+                    """,
+        SanitizerDefaults.DefaultOptions | RegexOptions.IgnorePatternWhitespace, SanitizerDefaults.DefaultMatchTimeoutMs)]
+    private static partial Regex PhoneRx();
+
+    [GeneratedRegex(@"\b\d{3}-\d{2}-\d{4}\b",
+        SanitizerDefaults.DefaultOptions, SanitizerDefaults.DefaultMatchTimeoutMs)]
+    private static partial Regex SsnRx();
+
+    [GeneratedRegex(@"\b\d{4}[-\s]?\d{4}[-\s]?\d{4}[-\s]?\d{4}\b",
+        SanitizerDefaults.DefaultOptions, SanitizerDefaults.DefaultMatchTimeoutMs)]
+    private static partial Regex CreditCardRx();
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/ProfilePathAndUsernameRuleProvider.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.Collections.Frozen;
+using System.Text.RegularExpressions;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+
+internal sealed class ProfilePathAndUsernameRuleProvider : ISanitizationRuleProvider
+{
+    private static readonly TimeSpan DefaultTimeout = TimeSpan.FromMilliseconds(SanitizerDefaults.DefaultMatchTimeoutMs);
+
+    private readonly Dictionary<string, string> _profilePaths = new(StringComparer.OrdinalIgnoreCase);
+    private readonly HashSet<string> _usernames = new(StringComparer.OrdinalIgnoreCase);
+
+    private static readonly FrozenSet<string> CommonPathParts = new HashSet<string>(StringComparer.OrdinalIgnoreCase)
+    {
+        "Users", "home", "Documents", "Desktop", "AppData", "Local", "Roaming",
+        "Pictures", "Videos", "Music", "Downloads", "Program Files", "Windows",
+        "System32", "bin", "usr", "var", "etc", "opt", "tmp",
+    }.ToFrozenSet(StringComparer.OrdinalIgnoreCase);
+
+    private static readonly FrozenSet<string> CommonWords = new HashSet<string>(StringComparer.OrdinalIgnoreCase)
+    {
+        "admin", "user", "test", "guest", "public", "system", "service",
+        "default", "temp", "local", "shared", "common", "data", "config",
+    }.ToFrozenSet(StringComparer.OrdinalIgnoreCase);
+
+    public ProfilePathAndUsernameRuleProvider()
+    {
+        DetectSystemPaths();
+    }
+
+    public IEnumerable<SanitizationRule> GetRules()
+    {
+        List<SanitizationRule> rules = [];
+
+        // Profile path rules (ordered longest-first)
+        var orderedRules = _profilePaths
+            .Where(p => !string.IsNullOrEmpty(p.Key))
+            .OrderByDescending(p => p.Key.Length);
+
+        foreach (var profilePath in orderedRules)
+        {
+            try
+            {
+                var normalizedPath = profilePath.Key
+                    .Replace('/', Path.DirectorySeparatorChar)
+                    .Replace('\\', Path.DirectorySeparatorChar);
+                var escapedPath = Regex.Escape(normalizedPath);
+
+                var pattern = escapedPath + @"(?:[/\\]*)";
+                var rx = new Regex(pattern, SanitizerDefaults.DefaultOptions, DefaultTimeout);
+
+                rules.Add(new(rx, profilePath.Value, $"Profile path: {profilePath}"));
+            }
+            catch
+            {
+                // Skip problematic paths
+            }
+        }
+
+        // Username rules
+        foreach (var username in _usernames.Where(u => !string.IsNullOrEmpty(u) && u.Length > 2))
+        {
+            try
+            {
+                if (!IsLikelyUsername(username))
+                {
+                    continue;
+                }
+
+                var rx = new Regex(@"\b" + Regex.Escape(username) + @"\b", SanitizerDefaults.DefaultOptions, DefaultTimeout);
+                rules.Add(new(rx, "[USERNAME_REDACTED]", $"Username: {username}"));
+            }
+            catch
+            {
+                // Skip problematic usernames
+            }
+        }
+
+        return rules;
+    }
+
+    public IReadOnlyDictionary<string, string> GetDetectedProfilePaths() => _profilePaths;
+
+    public IReadOnlyCollection<string> GetDetectedUsernames() => _usernames;
+
+    private void DetectSystemPaths()
+    {
+        try
+        {
+            var userProfile = Environment.GetFolderPath(Environment.SpecialFolder.UserProfile);
+            if (!string.IsNullOrEmpty(userProfile) && Directory.Exists(userProfile))
+            {
+                _profilePaths.Add(userProfile, "[USER_PROFILE_DIR]");
+                var username = Path.GetFileName(userProfile);
+                if (!string.IsNullOrEmpty(username) && username.Length > 2)
+                {
+                    _usernames.Add(username);
+                }
+            }
+
+            Environment.SpecialFolder[] profileFolders =
+            [
+                Environment.SpecialFolder.ApplicationData,
+                Environment.SpecialFolder.LocalApplicationData,
+                Environment.SpecialFolder.Desktop,
+                Environment.SpecialFolder.MyDocuments,
+                Environment.SpecialFolder.MyPictures,
+                Environment.SpecialFolder.MyVideos,
+                Environment.SpecialFolder.MyMusic,
+                Environment.SpecialFolder.StartMenu,
+                Environment.SpecialFolder.Startup,
+                Environment.SpecialFolder.DesktopDirectory
+            ];
+
+            foreach (var folder in profileFolders)
+            {
+                var dir = Environment.GetFolderPath(folder);
+                if (string.IsNullOrEmpty(dir))
+                {
+                    continue;
+                }
+
+                var added = _profilePaths.TryAdd(dir, $"[{folder.ToString().ToUpperInvariant()}_DIR]");
+                if (!added)
+                {
+                    continue;
+                }
+            }
+
+            string[] envVars = ["USERPROFILE", "HOME", "OneDrive", "OneDriveCommercial"];
+            foreach (var envVar in envVars)
+            {
+                var envPath = Environment.GetEnvironmentVariable(envVar);
+                if (!string.IsNullOrEmpty(envPath) && Directory.Exists(envPath))
+                {
+                    _profilePaths.TryAdd(envPath, $"[{envVar.ToUpperInvariant()}_DIR]");
+                }
+            }
+        }
+        catch (Exception ex)
+        {
+            CoreLogger.LogError("Error detecting system profile paths and usernames", ex);
+        }
+    }
+
+    private static bool IsLikelyUsername(string username) =>
+        !CommonWords.Contains(username) &&
+        username.Length is >= 3 and <= 50 &&
+        !username.All(char.IsDigit);
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/SanitizerDefaults.cs

@@ -0,0 +1,13 @@
+// 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.Text.RegularExpressions;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+
+internal static class SanitizerDefaults
+{
+    public const RegexOptions DefaultOptions = RegexOptions.IgnoreCase | RegexOptions.CultureInvariant | RegexOptions.Compiled;
+    public const int DefaultMatchTimeoutMs = 100;
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/SecretKeyValueRulesProvider.cs

@@ -0,0 +1,172 @@
+// Copyright (c) Microsoft Corporation
+// The Microsoft Corporation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+using System.Collections.Frozen;
+using System.Text.RegularExpressions;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+
+internal sealed class SecretKeyValueRulesProvider : ISanitizationRuleProvider
+{
+    // Central list of common secret keys/phrases to redact when found in key=value pairs.
+    private static readonly FrozenSet<string> SecretKeys = new HashSet<string>(StringComparer.OrdinalIgnoreCase)
+    {
+        // Core passwords/secrets
+        "password",
+        "passphrase",
+        "passwd",
+        "pwd",
+
+        // Tokens
+        "token",
+        "access token",
+        "refresh token",
+        "id token",
+        "auth token",
+        "session token",
+        "bearer token",
+        "personal access token",
+        "pat",
+
+        // API / client credentials
+        "api key",
+        "api secret",
+        "x api key",
+        "client id",
+        "client secret",
+        "x client id",
+        "x client secret",
+        "consumer secret",
+        "service principal secret",
+
+        // Cloud & platform (Azure/AppInsights/etc.)
+        "subscription key",
+        "instrumentation key",
+        "account key",
+        "storage account key",
+        "shared access key",
+        "shared access signature",
+        "SAS token",
+
+        // Connection strings (often surfaced in exception messages)
+        "connection string",
+        "conn string",
+        "storage connection string",
+
+        // Certificates & crypto
+        "private key",
+        "certificate password",
+        "client certificate password",
+        "pfx password",
+
+        // AWS common keys
+        "aws access key id",
+        "aws secret access key",
+        "aws session token",
+
+        // Optional service aliases
+        "cosmos db key",
+    }.ToFrozenSet(StringComparer.OrdinalIgnoreCase);
+
+    public IEnumerable<SanitizationRule> GetRules()
+    {
+        yield return BuildSecretKeyValueRule(
+            SecretKeys,
+            timeout: TimeSpan.FromSeconds(5),
+            starEverything: true);
+    }
+
+    private static SanitizationRule BuildSecretKeyValueRule(
+        IEnumerable<string> keys,
+        RegexOptions? options = null,
+        TimeSpan? timeout = null,
+        string label = "[REDACTED]",
+        bool treatDashUnderscoreAsSpace = true,
+        string separatorsClass = "[:=]",     // char class for separators
+        string unquotedStopClass = "\\s",
+        bool starEverything = false)
+    {
+        ArgumentNullException.ThrowIfNull(keys);
+
+        // Between-word matcher for keys: "api key" -> "api\s*key" (optionally treating _/- as "space")
+        var between = treatDashUnderscoreAsSpace ? @"(?:\s|[_-])*" : @"\s*";
+
+        var patterns = new List<string>();
+
+        foreach (var raw in keys)
+        {
+            var key = raw?.Trim();
+            if (string.IsNullOrEmpty(key))
+            {
+                continue;
+            }
+
+            if (starEverything && key is not ['*', ..])
+            {
+                key = "*" + key;
+            }
+
+            if (key is ['*', .. var tail])
+            {
+                // Wildcard prefix: allow one non-space token + optional "-" or "_" before the remainder.
+                // Matches: "api key", "api-key", "azure-api-key", "user_api_key"
+                var remainder = tail.Trim();
+                if (remainder.Length == 0)
+                {
+                    continue;
+                }
+
+                var rem = Normalize(remainder, between);
+                patterns.Add($@"(?:(?>[A-Za-z0-9_]{{1,128}}[_-]))?{rem}");
+            }
+            else
+            {
+                patterns.Add(Normalize(key, between));
+            }
+        }
+
+        if (patterns.Count == 0)
+        {
+            throw new ArgumentException("No non-empty keys provided.", nameof(keys));
+        }
+
+        var keysAlt = string.Join("|", patterns);
+
+        var pattern =
+            $"""
+             # Negative lookbehind to ensure the key is not part of a larger word
+             (?<![A-Za-z0-9])
+             # Match and capture the key (from the provided list)
+             (?<key>(?:{keysAlt}))
+             # Negative lookahead to ensure the key is not part of a larger word
+             (?![A-Za-z0-9])
+             # Optional whitespace between key and separator
+             \s*
+             # Separator (e.g., ':' or '=')
+             (?<sep>{separatorsClass})
+             # Optional whitespace after separator
+             \s*
+             # Match and capture the value, supporting quoted or unquoted values
+             (?:
+                 # Quoted value: match opening quote, value, and closing quote
+                 (?<q>["'])(?<val>[^"']+)\k<q>
+                 |
+                 # Unquoted value: match up to the next whitespace
+                 (?<val>[^{unquotedStopClass}]+)
+             )
+             """;
+
+        var rx = new Regex(
+            pattern,
+            (options ?? (RegexOptions.IgnoreCase | RegexOptions.CultureInvariant)) | RegexOptions.IgnorePatternWhitespace,
+            timeout ?? TimeSpan.FromMilliseconds(1000));
+
+        var replacement = @"${key}${sep} ${q}" + label + @"${q}";
+        return new SanitizationRule(rx, replacement, "Sensitive key/value pairs");
+
+        static string Normalize(string s, string betweenSep)
+            => Regex.Escape(s).Replace("\\ ", betweenSep);
+    }
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/TextSanitizer.cs

@@ -0,0 +1,135 @@
+// 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.Text.RegularExpressions;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+
+/// <summary>
+/// Generic text sanitizer that applies a sequence of regex-based rules over input text.
+/// </summary>
+internal sealed class TextSanitizer : ITextSanitizer
+{
+    // Default guardrail: sanitized text must retain at least 30% of the original length
+    private const double DefaultGuardrailThreshold = 0.3;
+    private static readonly TimeSpan DefaultTimeout = TimeSpan.FromMilliseconds(SanitizerDefaults.DefaultMatchTimeoutMs);
+
+    private readonly List<SanitizationRule> _rules = [];
+    private readonly double _guardrailThreshold;
+    private readonly Action<GuardrailEventArgs>? _onGuardrailTriggered;
+
+    public TextSanitizer(
+        double guardrailThreshold = DefaultGuardrailThreshold,
+        Action<GuardrailEventArgs>? onGuardrailTriggered = null)
+    {
+        _guardrailThreshold = guardrailThreshold;
+        _onGuardrailTriggered = onGuardrailTriggered;
+    }
+
+    public TextSanitizer(
+        IEnumerable<ISanitizationRuleProvider> providers,
+        double guardrailThreshold = DefaultGuardrailThreshold,
+        Action<GuardrailEventArgs>? onGuardrailTriggered = null)
+    {
+        ArgumentNullException.ThrowIfNull(providers);
+        _guardrailThreshold = guardrailThreshold;
+        _onGuardrailTriggered = onGuardrailTriggered;
+
+        foreach (var p in providers)
+        {
+            try
+            {
+                _rules.AddRange(p.GetRules());
+            }
+            catch
+            {
+                // Best-effort; ignore provider errors
+            }
+        }
+    }
+
+    public string Sanitize(string? input)
+    {
+        if (string.IsNullOrEmpty(input))
+        {
+            return input ?? string.Empty;
+        }
+
+        var result = input;
+
+        foreach (var rule in _rules)
+        {
+            try
+            {
+                var previous = result;
+
+                result = rule.Evaluator is null
+                    ? rule.Regex.Replace(previous, rule.Replacement!)
+                    : rule.Regex.Replace(previous, rule.Evaluator);
+
+                if (result.Length < previous.Length * _guardrailThreshold)
+                {
+                    _onGuardrailTriggered?.Invoke(new GuardrailEventArgs(
+                        rule.Description,
+                        previous.Length,
+                        result.Length,
+                        _guardrailThreshold));
+                    result = previous; // Guardrail
+                }
+            }
+            catch (RegexMatchTimeoutException)
+            {
+                // Ignore timeouts; keep the original input
+            }
+            catch
+            {
+                // Ignore other exceptions; keep the original input
+            }
+        }
+
+        return result;
+    }
+
+    public void AddRule(string pattern, string replacement, string description = "")
+    {
+        var rx = new Regex(pattern, SanitizerDefaults.DefaultOptions, DefaultTimeout);
+        _rules.Add(new SanitizationRule(rx, replacement, description));
+    }
+
+    public void RemoveRule(string description)
+    {
+        _rules.RemoveAll(r => r.Description.Equals(description, StringComparison.OrdinalIgnoreCase));
+    }
+
+    public IReadOnlyList<SanitizationRule> GetRules() => _rules.AsReadOnly();
+
+    public string TestRule(string input, string ruleDescription)
+    {
+        var rule = _rules.FirstOrDefault(r => r.Description.Contains(ruleDescription, StringComparison.OrdinalIgnoreCase));
+        if (rule.Regex is null)
+        {
+            return input;
+        }
+
+        try
+        {
+            if (rule.Evaluator is not null)
+            {
+                return rule.Regex.Replace(input, rule.Evaluator);
+            }
+
+            if (rule.Replacement is not null)
+            {
+                return rule.Regex.Replace(input, rule.Replacement);
+            }
+        }
+        catch
+        {
+            // Ignore exceptions; return original input
+        }
+
+        return input;
+    }
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/TokenRuleProvider.cs

@@ -0,0 +1,25 @@
+// 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.Text.RegularExpressions;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+
+internal sealed partial class TokenRuleProvider : ISanitizationRuleProvider
+{
+    public IEnumerable<SanitizationRule> GetRules()
+    {
+        yield return new(JwtRx(), "[JWT_REDACTED]", "JSON Web Tokens (JWT)");
+        yield return new(TokenRx(), "[TOKEN_REDACTED]", "Potential API keys/tokens");
+    }
+
+    [GeneratedRegex(@"\beyJ[A-Za-z0-9_-]{10,}\.[A-Za-z0-9_-]{10,}\.[A-Za-z0-9_-]{10,}\b",
+        SanitizerDefaults.DefaultOptions, SanitizerDefaults.DefaultMatchTimeoutMs)]
+    private static partial Regex JwtRx();
+
+    [GeneratedRegex(@"\b[A-Za-z0-9]{32,128}\b",
+        SanitizerDefaults.DefaultOptions, SanitizerDefaults.DefaultMatchTimeoutMs)]
+    private static partial Regex TokenRx();
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.Common/Services/Sanitizer/UrlRuleProvider.cs

@@ -0,0 +1,20 @@
+// 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.Text.RegularExpressions;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+
+internal sealed partial class UrlRuleProvider : ISanitizationRuleProvider
+{
+    public IEnumerable<SanitizationRule> GetRules()
+    {
+        yield return new(UrlRx(), "[URL_REDACTED]", "URLs");
+    }
+
+    [GeneratedRegex(@"\b(?:https?|ftp|ftps|file|jdbc|ldap|mailto)://[^\s<>""'{}\[\]\\^`|]+",
+        SanitizerDefaults.DefaultOptions, SanitizerDefaults.DefaultMatchTimeoutMs)]
+    private static partial Regex UrlRx();
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/BatchUpdateManager.cs

@@ -0,0 +1,136 @@
+// Copyright (c) Microsoft Corporation
+// The Microsoft Corporation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+using System.Collections.Concurrent;
+using Microsoft.CmdPal.Core.Common;
+using Microsoft.CmdPal.Core.Common.Helpers;
+
+namespace Microsoft.CmdPal.Core.ViewModels;
+
+internal static class BatchUpdateManager
+{
+    private const int ExpectedBatchSize = 32;
+
+    // 30 ms chosen empirically to balance responsiveness and batching:
+    // - Keeps perceived latency low (< ~50 ms) for user-visible updates.
+    // - Still allows multiple COM/background events to be coalesced into a single batch.
+    private static readonly TimeSpan BatchDelay = TimeSpan.FromMilliseconds(30);
+    private static readonly ConcurrentQueue<IBatchUpdateTarget> DirtyQueue = [];
+    private static readonly Timer Timer = new(static _ => Flush(), null, Timeout.InfiniteTimeSpan, Timeout.InfiniteTimeSpan);
+
+    private static InterlockedBoolean _isFlushScheduled;
+
+    /// <summary>
+    /// Enqueue a target for batched processing. Safe to call from any thread (including COM callbacks).
+    /// </summary>
+    public static void Queue(IBatchUpdateTarget target)
+    {
+        if (!target.TryMarkBatchQueued())
+        {
+            return; // already queued in current batch window
+        }
+
+        DirtyQueue.Enqueue(target);
+        TryScheduleFlush();
+    }
+
+    private static void TryScheduleFlush()
+    {
+        if (!_isFlushScheduled.Set())
+        {
+            return;
+        }
+
+        if (DirtyQueue.IsEmpty)
+        {
+            _isFlushScheduled.Clear();
+
+            if (DirtyQueue.IsEmpty)
+            {
+                return;
+            }
+
+            if (!_isFlushScheduled.Set())
+            {
+                return;
+            }
+        }
+
+        try
+        {
+            Timer.Change(BatchDelay, Timeout.InfiniteTimeSpan);
+        }
+        catch (Exception ex)
+        {
+            _isFlushScheduled.Clear();
+            CoreLogger.LogError("Failed to arm batch timer.", ex);
+        }
+    }
+
+    private static void Flush()
+    {
+        try
+        {
+            var drained = new List<IBatchUpdateTarget>(ExpectedBatchSize);
+            while (DirtyQueue.TryDequeue(out var item))
+            {
+                drained.Add(item);
+            }
+
+            if (drained.Count == 0)
+            {
+                return;
+            }
+
+            // LOAD BEARING:
+            // ApplyPendingUpdates must run on a background thread.
+            // The VM itself is responsible for marshaling UI notifications to its _uiScheduler.
+            ApplyBatch(drained);
+        }
+        catch (Exception ex)
+        {
+            // Don't kill the timer thread.
+            CoreLogger.LogError("Batch flush failed.", ex);
+        }
+        finally
+        {
+            _isFlushScheduled.Clear();
+            TryScheduleFlush();
+        }
+    }
+
+    private static void ApplyBatch(List<IBatchUpdateTarget> items)
+    {
+        // Runs on the Timer callback thread (ThreadPool). That's fine: background work only.
+        foreach (var item in items)
+        {
+            // Allow re-queueing immediately if more COM events arrive during apply.
+            item.ClearBatchQueued();
+
+            try
+            {
+                item.ApplyPendingUpdates();
+            }
+            catch (Exception ex)
+            {
+                CoreLogger.LogError("Failed to apply pending updates for a batched target.", ex);
+            }
+        }
+    }
+}
+
+internal interface IBatchUpdateTarget
+{
+    /// <summary>UI scheduler (used by targets internally for UI marshaling). Kept here for diagnostics / consistency.</summary>
+    TaskScheduler UIScheduler { get; }
+
+    /// <summary>Apply any coalesced updates. Must be safe to call on a background thread.</summary>
+    void ApplyPendingUpdates();
+
+    /// <summary>De-dupe gate: returns true only for the first enqueue until cleared.</summary>
+    bool TryMarkBatchQueued();
+
+    /// <summary>Clear the de-dupe gate so the item can be queued again.</summary>
+    void ClearBatchQueued();
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ContextMenuViewModel.cs

@@ -53,7 +53,7 @@ public partial class ContextMenuViewModel : ObservableObject,
     {
         if (SelectedItem is not null)
         {
-            if (SelectedItem.MoreCommands.Count() > 1)
+            if (SelectedItem.PrimaryCommand is not null || SelectedItem.HasMoreCommands)
             {
                 ContextMenuStack.Clear();
                 PushContextStack(SelectedItem.AllCommands);

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/ExtensionObjectViewModel.cs

@@ -2,36 +2,99 @@
 // 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.Buffers;
+using System.Collections.Concurrent;
+using System.ComponentModel;
+using System.Runtime.CompilerServices;
 using CommunityToolkit.Mvvm.ComponentModel;
 using Microsoft.CmdPal.Core.Common;
+using Microsoft.CmdPal.Core.Common.Helpers;
 
 namespace Microsoft.CmdPal.Core.ViewModels;
 
-public abstract partial class ExtensionObjectViewModel : ObservableObject
+public abstract partial class ExtensionObjectViewModel : ObservableObject, IBatchUpdateTarget, IBackgroundPropertyChangedNotification
 {
-    public WeakReference<IPageContext> PageContext { get; set; }
+    private const int InitialPropertyBatchingBufferSize = 16;
 
-    internal ExtensionObjectViewModel(IPageContext? context)
-    {
-        var realContext = context ?? (this is IPageContext c ? c : throw new ArgumentException("You need to pass in an IErrorContext"));
-        PageContext = new(realContext);
-    }
+    // Raised on the background thread before UI notifications. It's raised on the background thread to prevent
+    // blocking the COM proxy.
+    public event PropertyChangedEventHandler? PropertyChangedBackground;
 
-    internal ExtensionObjectViewModel(WeakReference<IPageContext> context)
-    {
-        PageContext = context;
-    }
+    private readonly ConcurrentQueue<string> _pendingProps = [];
 
-    public async virtual Task InitializePropertiesAsync()
+    private readonly TaskScheduler _uiScheduler;
+
+    private InterlockedBoolean _batchQueued;
+
+    public WeakReference<IPageContext> PageContext { get; private set; } = null!;
+
+    TaskScheduler IBatchUpdateTarget.UIScheduler => _uiScheduler;
+
+    void IBatchUpdateTarget.ApplyPendingUpdates() => ApplyPendingUpdates();
+
+    bool IBatchUpdateTarget.TryMarkBatchQueued() => _batchQueued.Set();
+
+    void IBatchUpdateTarget.ClearBatchQueued() => _batchQueued.Clear();
+
+    private protected ExtensionObjectViewModel(TaskScheduler scheduler)
     {
-        var t = new Task(() =>
+        if (this is not IPageContext)
         {
-            SafeInitializePropertiesSynchronous();
-        });
-        t.Start();
-        await t;
+            throw new InvalidOperationException($"Constructor overload without IPageContext can only be used when the derived class implements IPageContext. Type: {GetType().FullName}");
+        }
+
+        _uiScheduler = scheduler ?? throw new ArgumentNullException(nameof(scheduler));
+
+        // Defer PageContext assignment - derived constructor MUST call InitializePageContext()
+        // or we set it lazily on first access
     }
 
+    private protected ExtensionObjectViewModel(IPageContext context)
+    {
+        ArgumentNullException.ThrowIfNull(context);
+
+        PageContext = new WeakReference<IPageContext>(context);
+        _uiScheduler = context.Scheduler;
+
+        LogIfDefaultScheduler();
+    }
+
+    private protected ExtensionObjectViewModel(WeakReference<IPageContext> contextRef)
+    {
+        ArgumentNullException.ThrowIfNull(contextRef);
+
+        if (!contextRef.TryGetTarget(out var context))
+        {
+            throw new ArgumentException("IPageContext must be alive when creating view models.", nameof(contextRef));
+        }
+
+        PageContext = contextRef;
+        _uiScheduler = context.Scheduler;
+
+        LogIfDefaultScheduler();
+    }
+
+    protected void InitializeSelfAsPageContext()
+    {
+        if (this is not IPageContext self)
+        {
+            throw new InvalidOperationException("This method can only be called when the class implements IPageContext.");
+        }
+
+        PageContext = new WeakReference<IPageContext>(self);
+    }
+
+    private void LogIfDefaultScheduler()
+    {
+        if (_uiScheduler == TaskScheduler.Default)
+        {
+            CoreLogger.LogDebug($"ExtensionObjectViewModel created with TaskScheduler.Default. Type: {GetType().FullName}");
+        }
+    }
+
+    public virtual Task InitializePropertiesAsync()
+        => Task.Run(SafeInitializePropertiesSynchronous);
+
     public void SafeInitializePropertiesSynchronous()
     {
         try
@@ -46,49 +109,151 @@ public abstract partial class ExtensionObjectViewModel : ObservableObject
 
     public abstract void InitializeProperties();
 
-    protected void UpdateProperty(string propertyName)
-    {
-        DoOnUiThread(() => OnPropertyChanged(propertyName));
-    }
+    protected void UpdateProperty(string propertyName) => MarkPropertyDirty(propertyName);
 
     protected void UpdateProperty(string propertyName1, string propertyName2)
     {
-        DoOnUiThread(() =>
-        {
-            OnPropertyChanged(propertyName1);
-            OnPropertyChanged(propertyName2);
-        });
-    }
-
-    protected void UpdateProperty(string propertyName1, string propertyName2, string propertyName3)
-    {
-        DoOnUiThread(() =>
-        {
-            OnPropertyChanged(propertyName1);
-            OnPropertyChanged(propertyName2);
-            OnPropertyChanged(propertyName3);
-        });
+        MarkPropertyDirty(propertyName1);
+        MarkPropertyDirty(propertyName2);
     }
 
     protected void UpdateProperty(params string[] propertyNames)
     {
-        DoOnUiThread(() =>
+        foreach (var p in propertyNames)
         {
-            foreach (var propertyName in propertyNames)
-            {
-                OnPropertyChanged(propertyName);
-            }
-        });
+            MarkPropertyDirty(p);
+        }
     }
 
+    internal void MarkPropertyDirty(string? propertyName)
+    {
+        if (string.IsNullOrEmpty(propertyName))
+        {
+            return;
+        }
+
+        // We should re-consider if this worth deduping
+        _pendingProps.Enqueue(propertyName);
+        BatchUpdateManager.Queue(this);
+    }
+
+    public void ApplyPendingUpdates()
+    {
+        ((IBatchUpdateTarget)this).ClearBatchQueued();
+
+        var buffer = ArrayPool<string>.Shared.Rent(InitialPropertyBatchingBufferSize);
+        var count = 0;
+        var transferred = false;
+
+        try
+        {
+            while (_pendingProps.TryDequeue(out var name))
+            {
+                if (count == buffer.Length)
+                {
+                    var bigger = ArrayPool<string>.Shared.Rent(buffer.Length * 2);
+                    Array.Copy(buffer, bigger, buffer.Length);
+                    ArrayPool<string>.Shared.Return(buffer, clearArray: true);
+                    buffer = bigger;
+                }
+
+                buffer[count++] = name;
+            }
+
+            if (count == 0)
+            {
+                return;
+            }
+
+            // 1) Background subscribers (must be raised before UI notifications).
+            var propertyChangedEventHandler = PropertyChangedBackground;
+            if (propertyChangedEventHandler is not null)
+            {
+                RaiseBackground(propertyChangedEventHandler, this, buffer, count);
+            }
+
+            // 2) UI-facing PropertyChanged: ALWAYS marshal to UI scheduler.
+            // Hand-off pooled buffer to UI task (UI task returns it).
+            //
+            // It would be lovely to do nothing if no one is actually listening on PropertyChanged,
+            // but ObservableObject doesn't expose that information.
+            _ = Task.Factory.StartNew(
+                static state =>
+                {
+                    var p = (UiBatch)state!;
+                    try
+                    {
+                        p.Owner.RaiseUi(p.Names, p.Count);
+                    }
+                    catch (Exception ex)
+                    {
+                        CoreLogger.LogError("Failed to raise property change notifications on UI thread.", ex);
+                    }
+                    finally
+                    {
+                        ArrayPool<string>.Shared.Return(p.Names, clearArray: true);
+                    }
+                },
+                new UiBatch(this, buffer, count),
+                CancellationToken.None,
+                TaskCreationOptions.DenyChildAttach,
+                _uiScheduler);
+
+            transferred = true;
+        }
+        catch (Exception ex)
+        {
+            CoreLogger.LogError("Failed to apply pending property updates.", ex);
+        }
+        finally
+        {
+            if (!transferred)
+            {
+                ArrayPool<string>.Shared.Return(buffer, clearArray: true);
+            }
+        }
+    }
+
+    private void RaiseUi(string[] names, int count)
+    {
+        for (var i = 0; i < count; i++)
+        {
+            OnPropertyChanged(Args(names[i]));
+        }
+    }
+
+    private static void RaiseBackground(PropertyChangedEventHandler handlers, object sender, string[] names, int count)
+    {
+        try
+        {
+            for (var i = 0; i < count; i++)
+            {
+                handlers(sender, Args(names[i]));
+            }
+        }
+        catch (Exception ex)
+        {
+            CoreLogger.LogError("Failed to raise PropertyChangedBackground notifications.", ex);
+        }
+    }
+
+    private sealed record UiBatch(ExtensionObjectViewModel Owner, string[] Names, int Count);
+
     protected void ShowException(Exception ex, string? extensionHint = null)
     {
         if (PageContext.TryGetTarget(out var pageContext))
         {
             pageContext.ShowException(ex, extensionHint);
         }
+        else
+        {
+            CoreLogger.LogError("Failed to show exception because PageContext is no longer available.", ex);
+        }
     }
 
+    [MethodImpl(MethodImplOptions.AggressiveInlining)]
+    private static PropertyChangedEventArgs Args(string name) => new(name);
+
     protected void DoOnUiThread(Action action)
     {
         if (PageContext.TryGetTarget(out var pageContext))

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/IBackgroundPropertyChangedNotification.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.ComponentModel;
+
+namespace Microsoft.CmdPal.Core.ViewModels;
+
+/// <summary>
+/// Provides a notification mechanism for property changes that fires
+/// synchronously on the calling thread.
+/// </summary>
+public interface IBackgroundPropertyChangedNotification
+{
+    /// <summary>
+    /// Occurs when the value of a property changes.
+    /// </summary>
+    event PropertyChangedEventHandler? PropertyChangedBackground;
+}

src/modules/cmdpal/Core/Microsoft.CmdPal.Core.ViewModels/PageViewModel.cs

@@ -77,11 +77,11 @@ public partial class PageViewModel : ExtensionObjectViewModel, IPageContext
     public IconInfoViewModel Icon { get; protected set; }
 
     public PageViewModel(IPage? model, TaskScheduler scheduler, AppExtensionHost extensionHost)
-        : base((IPageContext?)null)
+        : base(scheduler)
     {
+        InitializeSelfAsPageContext();
         _pageModel = new(model);
         Scheduler = scheduler;
-        PageContext = new(this);
         ExtensionHost = extensionHost;
         Icon = new(null);
 

src/modules/cmdpal/CoreCommonProps.props

@@ -43,4 +43,10 @@
     </EmbeddedResource>
   </ItemGroup>
 
+  <ItemGroup>
+    <AssemblyAttribute Include="System.Runtime.CompilerServices.InternalsVisibleToAttribute">
+       <_Parameter1>$(AssemblyName).UnitTests</_Parameter1>
+    </AssemblyAttribute>
+  </ItemGroup>
+
 </Project>

src/modules/cmdpal/Microsoft.CmdPal.Ext.PowerToys.slnf

@@ -0,0 +1,26 @@
+{
+  "solution": {
+    "path": "..\\..\\..\\PowerToys.slnx",
+    "projects": [
+      "src\\common\\Common.Search\\Common.Search.csproj",
+      "src\\common\\Common.UI\\Common.UI.csproj",
+      "src\\common\\ManagedCommon\\ManagedCommon.csproj",
+      "src\\common\\ManagedTelemetry\\Telemetry\\ManagedTelemetry.csproj",
+      "src\\common\\PowerToys.ModuleContracts\\PowerToys.ModuleContracts.csproj",
+      "src\\common\\SettingsAPI\\SettingsAPI.vcxproj",
+      "src\\common\\interop\\PowerToys.Interop.vcxproj",
+      "src\\common\\logger\\logger.vcxproj",
+      "src\\common\\version\\version.vcxproj",
+      "src\\logging\\logging.vcxproj",
+      "src\\modules\\MouseUtils\\MouseJump.Common\\MouseJump.Common.csproj",
+      "src\\modules\\Workspaces\\Workspaces.ModuleServices\\Workspaces.ModuleServices.csproj",
+      "src\\modules\\Workspaces\\WorkspacesCsharpLibrary\\WorkspacesCsharpLibrary.csproj",
+      "src\\modules\\ZoomIt\\ZoomItSettingsInterop\\ZoomItSettingsInterop.vcxproj",
+      "src\\modules\\awake\\Awake.ModuleServices\\Awake.ModuleServices.csproj",
+      "src\\modules\\cmdpal\\ext\\Microsoft.CmdPal.Ext.PowerToys\\Microsoft.CmdPal.Ext.PowerToys.csproj",
+      "src\\modules\\colorPicker\\ColorPicker.ModuleServices\\ColorPicker.ModuleServices.csproj",
+      "src\\modules\\fancyzones\\FancyZonesEditorCommon\\FancyZonesEditorCommon.csproj",
+      "src\\settings-ui\\Settings.UI.Library\\Settings.UI.Library.csproj"
+    ]
+  }
+}

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

@@ -6,6 +6,7 @@ using ManagedCommon;
 using Microsoft.CmdPal.Core.Common.Services;
 using Microsoft.CmdPal.Core.ViewModels;
 using Microsoft.CmdPal.Core.ViewModels.Models;
+using Microsoft.CmdPal.UI.ViewModels.Services;
 using Microsoft.CommandPalette.Extensions;
 using Microsoft.Extensions.DependencyInjection;
 
@@ -23,6 +24,8 @@ public sealed class CommandProviderWrapper
 
     private readonly TaskScheduler _taskScheduler;
 
+    private readonly ICommandProviderCache? _commandProviderCache;
+
     public TopLevelViewModel[] TopLevelItems { get; private set; } = [];
 
     public TopLevelViewModel[] FallbackItems { get; private set; } = [];
@@ -43,13 +46,7 @@ public sealed class CommandProviderWrapper
 
     public bool IsActive { get; private set; }
 
-    public string ProviderId
-    {
-        get
-        {
-            return string.IsNullOrEmpty(Extension?.ExtensionUniqueId) ? Id : Extension.ExtensionUniqueId;
-        }
-    }
+    public string ProviderId => string.IsNullOrEmpty(Extension?.ExtensionUniqueId) ? Id : Extension.ExtensionUniqueId;
 
     public CommandProviderWrapper(ICommandProvider provider, TaskScheduler mainThread)
     {
@@ -77,9 +74,11 @@ public sealed class CommandProviderWrapper
         Logger.LogDebug($"Initialized command provider {ProviderId}");
     }
 
-    public CommandProviderWrapper(IExtensionWrapper extension, TaskScheduler mainThread)
+    public CommandProviderWrapper(IExtensionWrapper extension, TaskScheduler mainThread, ICommandProviderCache commandProviderCache)
     {
         _taskScheduler = mainThread;
+        _commandProviderCache = commandProviderCache;
+
         Extension = extension;
         ExtensionHost = new CommandPaletteHost(extension);
         if (!Extension.IsRunning())
@@ -128,30 +127,31 @@ public sealed class CommandProviderWrapper
         if (!isValid)
         {
             IsActive = false;
+            RecallFromCache();
             return;
         }
 
         var settings = serviceProvider.GetService<SettingsModel>()!;
 
-        IsActive = GetProviderSettings(settings).IsEnabled;
+        var providerSettings = GetProviderSettings(settings);
+        IsActive = providerSettings.IsEnabled;
         if (!IsActive)
         {
+            RecallFromCache();
             return;
         }
 
-        ICommandItem[]? commands = null;
-        IFallbackCommandItem[]? fallbacks = null;
-
+        var displayInfoInitialized = false;
         try
         {
             var model = _commandProvider.Unsafe!;
 
-            Task<ICommandItem[]> t = new(model.TopLevelCommands);
-            t.Start();
-            commands = await t.ConfigureAwait(false);
+            Task<ICommandItem[]> loadTopLevelCommandsTask = new(model.TopLevelCommands);
+            loadTopLevelCommandsTask.Start();
+            var commands = await loadTopLevelCommandsTask.ConfigureAwait(false);
 
             // On a BG thread here
-            fallbacks = model.FallbackCommands();
+            var fallbacks = model.FallbackCommands();
 
             if (model is ICommandProvider2 two)
             {
@@ -162,6 +162,13 @@ public sealed class CommandProviderWrapper
             DisplayName = model.DisplayName;
             Icon = new(model.Icon);
             Icon.InitializeProperties();
+            displayInfoInitialized = true;
+
+            // Update cached display name
+            if (_commandProviderCache is not null && Extension?.ExtensionUniqueId is not null)
+            {
+                _commandProviderCache.Memorize(Extension.ExtensionUniqueId, new CommandProviderCacheItem(model.DisplayName));
+            }
 
             // Note: explicitly not InitializeProperties()ing the settings here. If
             // we do that, then we'd regress GH #38321
@@ -177,6 +184,25 @@ public sealed class CommandProviderWrapper
             Logger.LogError("Failed to load commands from extension");
             Logger.LogError($"Extension was {Extension!.PackageFamilyName}");
             Logger.LogError(e.ToString());
+
+            if (!displayInfoInitialized)
+            {
+                RecallFromCache();
+            }
+        }
+    }
+
+    private void RecallFromCache()
+    {
+        var cached = _commandProviderCache?.Recall(ProviderId);
+        if (cached is not null)
+        {
+            DisplayName = cached.DisplayName;
+        }
+
+        if (string.IsNullOrWhiteSpace(DisplayName))
+        {
+            DisplayName = Extension?.PackageDisplayName ?? Extension?.PackageFamilyName ?? ProviderId;
         }
     }
 
@@ -185,7 +211,7 @@ public sealed class CommandProviderWrapper
         var settings = serviceProvider.GetService<SettingsModel>()!;
         var providerSettings = GetProviderSettings(settings);
 
-        Func<ICommandItem?, bool, TopLevelViewModel> makeAndAdd = (ICommandItem? i, bool fallback) =>
+        var makeAndAdd = (ICommandItem? i, bool fallback) =>
         {
             CommandItemViewModel commandItemViewModel = new(new(i), pageContext);
             TopLevelViewModel topLevelViewModel = new(commandItemViewModel, fallback, ExtensionHost, ProviderId, settings, providerSettings, serviceProvider, i);

src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Commands/OpenSettingsCommand.cs

@@ -19,7 +19,7 @@ public partial class OpenSettingsCommand : InvokableCommand
 
     public override ICommandResult Invoke()
     {
-        WeakReferenceMessenger.Default.Send<OpenSettingsMessage>();
+        WeakReferenceMessenger.Default.Send(new OpenSettingsMessage());
         return CommandResult.KeepOpen();
     }
 }

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

@@ -4,6 +4,4 @@
 
 namespace Microsoft.CmdPal.UI.Messages;
 
-public record OpenSettingsMessage()
-{
-}
+public record OpenSettingsMessage(string SettingsPageTag = "");

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

@@ -14,11 +14,13 @@ namespace Microsoft.CmdPal.UI.ViewModels;
 
 public partial class ProviderSettingsViewModel : ObservableObject
 {
+    private static readonly IconInfoViewModel EmptyIcon = new(null);
+
     private readonly CommandProviderWrapper _provider;
     private readonly ProviderSettings _providerSettings;
     private readonly SettingsModel _settings;
-
     private readonly Lock _initializeSettingsLock = new();
+
     private Task? _initializeSettingsTask;
 
     public ProviderSettingsViewModel(
@@ -43,7 +45,7 @@ public partial class ProviderSettingsViewModel : ObservableObject
         HasFallbackCommands ?
             $"{ExtensionName}, {TopLevelCommands.Count} commands, {_provider.FallbackItems?.Length} fallback commands" :
             $"{ExtensionName}, {TopLevelCommands.Count} commands" :
-        Resources.builtin_disabled_extension;
+        $"{ExtensionName}, {Resources.builtin_disabled_extension}";
 
     [MemberNotNullWhen(true, nameof(Extension))]
     public bool IsFromExtension => _provider.Extension is not null;
@@ -52,7 +54,7 @@ public partial class ProviderSettingsViewModel : ObservableObject
 
     public string ExtensionVersion => IsFromExtension ? $"{Extension.Version.Major}.{Extension.Version.Minor}.{Extension.Version.Build}.{Extension.Version.Revision}" : string.Empty;
 
-    public IconInfoViewModel Icon => _provider.Icon;
+    public IconInfoViewModel Icon => IsEnabled ? _provider.Icon : EmptyIcon;
 
     [ObservableProperty]
     public partial bool LoadingSettings { get; set; }
@@ -69,6 +71,7 @@ public partial class ProviderSettingsViewModel : ObservableObject
                 WeakReferenceMessenger.Default.Send<ReloadCommandsMessage>(new());
                 OnPropertyChanged(nameof(IsEnabled));
                 OnPropertyChanged(nameof(ExtensionSubtext));
+                OnPropertyChanged(nameof(Icon));
             }
 
             if (value == true)

src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Services/CommandProviderCacheContainer.cs

@@ -0,0 +1,10 @@
+// Copyright (c) Microsoft Corporation
+// The Microsoft Corporation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+namespace Microsoft.CmdPal.UI.ViewModels.Services;
+
+internal sealed class CommandProviderCacheContainer
+{
+    public Dictionary<string, CommandProviderCacheItem> Cache { get; init; } = new(StringComparer.Ordinal);
+}

src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Services/CommandProviderCacheItem.cs

@@ -0,0 +1,7 @@
+// Copyright (c) Microsoft Corporation
+// The Microsoft Corporation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+namespace Microsoft.CmdPal.UI.ViewModels.Services;
+
+public record CommandProviderCacheItem(string DisplayName);

src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Services/CommandProviderCacheSerializationContext.cs

@@ -0,0 +1,13 @@
+// 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.Text.Json.Serialization;
+
+namespace Microsoft.CmdPal.UI.ViewModels.Services;
+
+[JsonSerializable(typeof(CommandProviderCacheItem))]
+[JsonSerializable(typeof(Dictionary<string, CommandProviderCacheItem>))]
+[JsonSerializable(typeof(CommandProviderCacheContainer))]
+[JsonSourceGenerationOptions(WriteIndented = true, PropertyNameCaseInsensitive = false)]
+internal sealed partial class CommandProviderCacheSerializationContext : JsonSerializerContext;

src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Services/DefaultCommandProviderCache.cs

@@ -0,0 +1,127 @@
+// 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.Text.Json;
+using ManagedCommon;
+using Microsoft.CmdPal.Core.Common.Helpers;
+using Microsoft.CommandPalette.Extensions.Toolkit;
+
+namespace Microsoft.CmdPal.UI.ViewModels.Services;
+
+public sealed partial class DefaultCommandProviderCache : ICommandProviderCache, IDisposable
+{
+    private const string CacheFileName = "commandProviderCache.json";
+
+    private readonly Dictionary<string, CommandProviderCacheItem> _cache = new(StringComparer.Ordinal);
+
+    private readonly Lock _sync = new();
+
+    private readonly SupersedingAsyncGate _saveGate;
+
+    public DefaultCommandProviderCache()
+    {
+        _saveGate = new SupersedingAsyncGate(async _ => await TrySaveAsync().ConfigureAwait(false));
+        TryLoad();
+    }
+
+    public void Memorize(string providerId, CommandProviderCacheItem item)
+    {
+        ArgumentNullException.ThrowIfNull(providerId);
+
+        lock (_sync)
+        {
+            _cache[providerId] = item;
+        }
+
+        _ = _saveGate.ExecuteAsync();
+    }
+
+    public CommandProviderCacheItem? Recall(string providerId)
+    {
+        ArgumentNullException.ThrowIfNull(providerId);
+
+        lock (_sync)
+        {
+            _cache.TryGetValue(providerId, out var item);
+            return item;
+        }
+    }
+
+    private static string GetCacheFilePath()
+    {
+        var directory = Utilities.BaseSettingsPath("Microsoft.CmdPal");
+        Directory.CreateDirectory(directory);
+        return Path.Combine(directory, CacheFileName);
+    }
+
+    private void TryLoad()
+    {
+        try
+        {
+            var path = GetCacheFilePath();
+            if (!File.Exists(path))
+            {
+                return;
+            }
+
+            var json = File.ReadAllText(path);
+            if (string.IsNullOrWhiteSpace(json))
+            {
+                return;
+            }
+
+            var loaded = JsonSerializer.Deserialize(
+                json,
+                CommandProviderCacheSerializationContext.Default.CommandProviderCacheContainer!);
+            if (loaded?.Cache is null)
+            {
+                return;
+            }
+
+            _cache.Clear();
+            foreach (var kvp in loaded.Cache)
+            {
+                if (!string.IsNullOrEmpty(kvp.Key) && kvp.Value is not null)
+                {
+                    _cache[kvp.Key] = kvp.Value;
+                }
+            }
+        }
+        catch (Exception ex)
+        {
+            Logger.LogError("Failed to load command provider cache: ", ex);
+        }
+    }
+
+    private async Task TrySaveAsync()
+    {
+        try
+        {
+            Dictionary<string, CommandProviderCacheItem> snapshot;
+            lock (_sync)
+            {
+                snapshot = new Dictionary<string, CommandProviderCacheItem>(_cache, StringComparer.Ordinal);
+            }
+
+            var container = new CommandProviderCacheContainer
+            {
+                Cache = snapshot,
+            };
+
+            var path = GetCacheFilePath();
+            var json = JsonSerializer.Serialize(container, CommandProviderCacheSerializationContext.Default.CommandProviderCacheContainer!);
+            await File.WriteAllTextAsync(path, json).ConfigureAwait(false);
+        }
+        catch (Exception ex)
+        {
+            Logger.LogError("Failed to save command provider cache: ", ex);
+        }
+    }
+
+    public void Dispose()
+    {
+        _saveGate.Dispose();
+        GC.SuppressFinalize(this);
+    }
+}

src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Services/ICommandProviderCache.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.UI.ViewModels.Services;
+
+public interface ICommandProviderCache
+{
+    void Memorize(string providerId, CommandProviderCacheItem item);
+
+    CommandProviderCacheItem? Recall(string providerId);
+}

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

@@ -13,6 +13,7 @@ using Microsoft.CmdPal.Core.Common.Helpers;
 using Microsoft.CmdPal.Core.Common.Services;
 using Microsoft.CmdPal.Core.ViewModels;
 using Microsoft.CmdPal.UI.ViewModels.Messages;
+using Microsoft.CmdPal.UI.ViewModels.Services;
 using Microsoft.CommandPalette.Extensions;
 using Microsoft.CommandPalette.Extensions.Toolkit;
 using Microsoft.Extensions.DependencyInjection;
@@ -25,6 +26,7 @@ public partial class TopLevelCommandManager : ObservableObject,
     IDisposable
 {
     private readonly IServiceProvider _serviceProvider;
+    private readonly ICommandProviderCache _commandProviderCache;
     private readonly TaskScheduler _taskScheduler;
 
     private readonly List<CommandProviderWrapper> _builtInCommands = [];
@@ -34,9 +36,10 @@ public partial class TopLevelCommandManager : ObservableObject,
 
     TaskScheduler IPageContext.Scheduler => _taskScheduler;
 
-    public TopLevelCommandManager(IServiceProvider serviceProvider)
+    public TopLevelCommandManager(IServiceProvider serviceProvider, ICommandProviderCache commandProviderCache)
     {
         _serviceProvider = serviceProvider;
+        _commandProviderCache = commandProviderCache;
         _taskScheduler = _serviceProvider.GetService<TaskScheduler>()!;
         WeakReferenceMessenger.Default.Register<ReloadCommandsMessage>(this);
         _reloadCommandsGate = new(ReloadAllCommandsAsyncCore);
@@ -319,7 +322,7 @@ public partial class TopLevelCommandManager : ObservableObject,
         try
         {
             await extension.StartExtensionAsync().WaitAsync(TimeSpan.FromSeconds(10));
-            return new CommandProviderWrapper(extension, _taskScheduler);
+            return new CommandProviderWrapper(extension, _taskScheduler, _commandProviderCache);
         }
         catch (Exception ex)
         {

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

@@ -199,7 +199,7 @@ public sealed partial class TopLevelViewModel : ObservableObject, IListItem, IEx
             _fallbackId = fallback.Id;
         }
 
-        item.PropertyChanged += Item_PropertyChanged;
+        item.PropertyChangedBackground += Item_PropertyChanged;
 
         // UpdateAlias();
         // UpdateHotkey();

src/modules/cmdpal/Microsoft.CmdPal.UI/App.xaml.cs

@@ -41,7 +41,7 @@ namespace Microsoft.CmdPal.UI;
 /// <summary>
 /// Provides application-specific behavior to supplement the default Application class.
 /// </summary>
-public partial class App : Application
+public partial class App : Application, IDisposable
 {
     private readonly GlobalErrorHandler _globalErrorHandler = new();
 
@@ -67,7 +67,7 @@ public partial class App : Application
     public App()
     {
 #if !CMDPAL_DISABLE_GLOBAL_ERROR_HANDLER
-        _globalErrorHandler.Register(this);
+        _globalErrorHandler.Register(this, GlobalErrorHandler.Options.Default);
 #endif
 
         Services = ConfigureServices();
@@ -178,6 +178,7 @@ public partial class App : Application
         services.AddSingleton(state);
 
         // Services
+        services.AddSingleton<ICommandProviderCache, DefaultCommandProviderCache>();
         services.AddSingleton<TopLevelCommandManager>();
         services.AddSingleton<AliasManager>();
         services.AddSingleton<HotkeyManager>();
@@ -203,4 +204,11 @@ public partial class App : Application
         services.AddSingleton<ShellViewModel>();
         services.AddSingleton<IPageViewModelFactoryService, CommandPalettePageViewModelFactory>();
     }
+
+    public void Dispose()
+    {
+        _globalErrorHandler.Dispose();
+        EtwTrace.Dispose();
+        GC.SuppressFinalize(this);
+    }
 }

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

@@ -44,13 +44,14 @@ public sealed partial class CommandBar : UserControl,
 
     public void Receive(OpenContextMenuMessage message)
     {
-        if (!ViewModel.ShouldShowContextMenu)
-        {
-            return;
-        }
-
         if (message.Element is null)
         {
+            // This is invoked from the "More" button on the command bar
+            if (!ViewModel.ShouldShowContextMenu)
+            {
+                return;
+            }
+
             _ = DispatcherQueue.TryEnqueue(
                 () =>
                 {
@@ -65,6 +66,7 @@ public sealed partial class CommandBar : UserControl,
         }
         else
         {
+            // This is invoked from a specific element
             _ = DispatcherQueue.TryEnqueue(
             () =>
             {
@@ -126,7 +128,7 @@ public sealed partial class CommandBar : UserControl,
 
     private void SettingsIcon_Clicked(object sender, RoutedEventArgs e)
     {
-        WeakReferenceMessenger.Default.Send<OpenSettingsMessage>();
+        WeakReferenceMessenger.Default.Send(new OpenSettingsMessage());
     }
 
     private void MoreCommandsButton_Clicked(object sender, RoutedEventArgs e)

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

@@ -203,6 +203,12 @@
 
                                     </Grid>
                                 </Border>
+
+                                <!--  More section  -->
+                                <TextBlock Style="{ThemeResource SettingsSectionHeaderTextBlockStyle}" Text="More" />
+                                <Border>
+                                    <Button Command="{x:Bind ViewModel.OpenInternalToolsCommand}" Content="Open internal tools" />
+                                </Border>
                             </StackPanel>
 
                             <!--  Footer  -->

src/modules/cmdpal/Microsoft.CmdPal.UI/Helpers/GlobalErrorHandler.cs

@@ -3,7 +3,7 @@
 // See the LICENSE file in the project root for more information.
 
 using ManagedCommon;
-using Microsoft.CmdPal.Core.Common.Helpers;
+using Microsoft.CmdPal.Core.Common.Services.Reports;
 using Windows.Win32;
 using Windows.Win32.Foundation;
 using Windows.Win32.UI.WindowsAndMessaging;
@@ -15,14 +15,22 @@ namespace Microsoft.CmdPal.UI.Helpers;
 /// <summary>
 /// Global error handler for Command Palette.
 /// </summary>
-internal sealed partial class GlobalErrorHandler
+internal sealed partial class GlobalErrorHandler : IDisposable
 {
+    private readonly ErrorReportBuilder _errorReportBuilder = new();
+    private Options? _options;
+    private App? _app;
+
     // GlobalErrorHandler is designed to be self-contained; it can be registered and invoked before a service provider is available.
-    internal void Register(App app)
+    internal void Register(App app, Options options)
     {
         ArgumentNullException.ThrowIfNull(app);
+        ArgumentNullException.ThrowIfNull(options);
 
-        app.UnhandledException += App_UnhandledException;
+        _options = options;
+
+        _app = app;
+        _app.UnhandledException += App_UnhandledException;
         TaskScheduler.UnobservedTaskException += TaskScheduler_UnobservedTaskException;
         AppDomain.CurrentDomain.UnhandledException += CurrentDomain_UnhandledException;
     }
@@ -54,21 +62,15 @@ internal sealed partial class GlobalErrorHandler
         HandleException(e.Exception, Context.UnobservedTaskException);
     }
 
-    private static void HandleException(Exception ex, Context context)
+    private void HandleException(Exception ex, Context context)
     {
         Logger.LogError($"Unhandled exception detected ({context})", ex);
 
         if (context == Context.MainThreadException)
         {
-            var error = DiagnosticsHelper.BuildExceptionMessage(ex, null);
-            var report = $"""
-                          This is an error report generated by Windows Command Palette.
-                          If you are seeing this message, it means the application has encountered an unexpected issue.
-                          You can help us fix it by filing a report at https://aka.ms/powerToysReportBug.
-                          {error}
-                          """;
+            var report = _errorReportBuilder.BuildReport(ex, context.ToString(), _options?.RedactPii ?? true);
 
-            StoreReport(report, storeOnDesktop: false);
+            StoreReport(report, storeOnDesktop: _options?.StoreReportOnUserDesktop == true);
 
             string message;
             string caption;
@@ -138,6 +140,13 @@ internal sealed partial class GlobalErrorHandler
         }
     }
 
+    public void Dispose()
+    {
+        _app?.UnhandledException -= App_UnhandledException;
+        TaskScheduler.UnobservedTaskException -= TaskScheduler_UnobservedTaskException;
+        AppDomain.CurrentDomain.UnhandledException -= CurrentDomain_UnhandledException;
+    }
+
     private enum Context
     {
         Unknown = 0,
@@ -146,4 +155,26 @@ internal sealed partial class GlobalErrorHandler
         UnobservedTaskException,
         AppDomainUnhandledException,
     }
+
+    /// <summary>
+    /// Configuration options controlling how <see cref="GlobalErrorHandler"/> reacts to exceptions
+    /// (what to log, what to show to the user, and where to store reports).
+    /// </summary>
+    internal sealed record Options
+    {
+        /// <summary>
+        /// Gets the default configuration.
+        /// </summary>
+        public static Options Default { get; } = new();
+
+        /// <summary>
+        /// Gets a value indicating whether Personally Identifiable Information (PII) should be redacted in error reports.
+        /// </summary>
+        public bool RedactPii { get; init; } = true;
+
+        /// <summary>
+        /// Gets a value indicating whether to store the error report on the user's desktop in addition to the log directory.
+        /// </summary>
+        public bool StoreReportOnUserDesktop { get; init; }
+    }
 }

src/modules/cmdpal/Microsoft.CmdPal.UI/Helpers/TrayIconService.cs

@@ -152,7 +152,7 @@ internal sealed partial class TrayIconService
                 {
                     if (wParam == PInvoke.WM_USER + 1)
                     {
-                        WeakReferenceMessenger.Default.Send<OpenSettingsMessage>();
+                        WeakReferenceMessenger.Default.Send(new OpenSettingsMessage());
                     }
                     else if (wParam == PInvoke.WM_USER + 2)
                     {

src/modules/cmdpal/Microsoft.CmdPal.UI/Helpers/WindowPositionHelper.cs

@@ -0,0 +1,152 @@
+// 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.UI;
+using Microsoft.UI.Windowing;
+using Windows.Graphics;
+using Windows.Win32;
+using Windows.Win32.Graphics.Gdi;
+using Windows.Win32.UI.HiDpi;
+
+namespace Microsoft.CmdPal.UI.Helpers;
+
+internal static class WindowPositionHelper
+{
+    private const int DefaultWidth = 800;
+    private const int DefaultHeight = 480;
+    private const int MinimumVisibleSize = 100;
+    private const int DefaultDpi = 96;
+
+    public static PointInt32? CalculateCenteredPosition(DisplayArea? displayArea, SizeInt32 windowSize, int windowDpi)
+    {
+        if (displayArea is null)
+        {
+            return null;
+        }
+
+        var workArea = displayArea.WorkArea;
+        if (workArea.Width <= 0 || workArea.Height <= 0)
+        {
+            return null;
+        }
+
+        var targetDpi = GetDpiForDisplay(displayArea);
+        var predictedSize = ScaleSize(windowSize, windowDpi, targetDpi);
+
+        // Clamp to work area
+        var width = Math.Min(predictedSize.Width, workArea.Width);
+        var height = Math.Min(predictedSize.Height, workArea.Height);
+
+        return new PointInt32(
+            workArea.X + ((workArea.Width - width) / 2),
+            workArea.Y + ((workArea.Height - height) / 2));
+    }
+
+    /// <summary>
+    /// Adjusts a saved window rect to ensure it's visible on the nearest display,
+    /// accounting for DPI changes and work area differences.
+    /// </summary>
+    ///
+    public static RectInt32 AdjustRectForVisibility(RectInt32 savedRect, SizeInt32 savedScreenSize, int savedDpi)
+    {
+        var displayArea = DisplayArea.GetFromRect(savedRect, DisplayAreaFallback.Nearest);
+        if (displayArea is null)
+        {
+            return savedRect;
+        }
+
+        var workArea = displayArea.WorkArea;
+        if (workArea.Width <= 0 || workArea.Height <= 0)
+        {
+            return savedRect;
+        }
+
+        var targetDpi = GetDpiForDisplay(displayArea);
+        if (savedDpi <= 0)
+        {
+            savedDpi = targetDpi;
+        }
+
+        var hasInvalidSize = savedRect.Width <= 0 || savedRect.Height <= 0;
+        if (hasInvalidSize)
+        {
+            savedRect = savedRect with { Width = DefaultWidth, Height = DefaultHeight };
+        }
+
+        if (targetDpi != savedDpi)
+        {
+            savedRect = ScaleRect(savedRect, savedDpi, targetDpi);
+        }
+
+        var clampedSize = ClampSize(savedRect.Width, savedRect.Height, workArea);
+
+        var shouldRecenter = hasInvalidSize ||
+                             IsOffscreen(savedRect, workArea) ||
+                             savedScreenSize.Width != workArea.Width ||
+                             savedScreenSize.Height != workArea.Height;
+
+        if (shouldRecenter)
+        {
+            return CenterRectInWorkArea(clampedSize, workArea);
+        }
+
+        return new RectInt32(savedRect.X, savedRect.Y, clampedSize.Width, clampedSize.Height);
+    }
+
+    private static int GetDpiForDisplay(DisplayArea displayArea)
+    {
+        var hMonitor = Win32Interop.GetMonitorFromDisplayId(displayArea.DisplayId);
+        if (hMonitor == IntPtr.Zero)
+        {
+            return DefaultDpi;
+        }
+
+        var hr = PInvoke.GetDpiForMonitor(
+            new HMONITOR(hMonitor),
+            MONITOR_DPI_TYPE.MDT_EFFECTIVE_DPI,
+            out var dpiX,
+            out _);
+
+        return hr.Succeeded && dpiX > 0 ? (int)dpiX : DefaultDpi;
+    }
+
+    private static SizeInt32 ScaleSize(SizeInt32 size, int fromDpi, int toDpi)
+    {
+        if (fromDpi <= 0 || toDpi <= 0 || fromDpi == toDpi)
+        {
+            return size;
+        }
+
+        var scale = (double)toDpi / fromDpi;
+        return new SizeInt32(
+            (int)Math.Round(size.Width * scale),
+            (int)Math.Round(size.Height * scale));
+    }
+
+    private static RectInt32 ScaleRect(RectInt32 rect, int fromDpi, int toDpi)
+    {
+        var scale = (double)toDpi / fromDpi;
+        return new RectInt32(
+            (int)Math.Round(rect.X * scale),
+            (int)Math.Round(rect.Y * scale),
+            (int)Math.Round(rect.Width * scale),
+            (int)Math.Round(rect.Height * scale));
+    }
+
+    private static SizeInt32 ClampSize(int width, int height, RectInt32 workArea) =>
+        new(Math.Min(width, workArea.Width), Math.Min(height, workArea.Height));
+
+    private static RectInt32 CenterRectInWorkArea(SizeInt32 size, RectInt32 workArea) =>
+        new(
+            workArea.X + ((workArea.Width - size.Width) / 2),
+            workArea.Y + ((workArea.Height - size.Height) / 2),
+            size.Width,
+            size.Height);
+
+    private static bool IsOffscreen(RectInt32 rect, RectInt32 workArea) =>
+        rect.X + MinimumVisibleSize > workArea.X + workArea.Width ||
+        rect.X + rect.Width - MinimumVisibleSize < workArea.X ||
+        rect.Y + MinimumVisibleSize > workArea.Y + workArea.Height ||
+        rect.Y + rect.Height - MinimumVisibleSize < workArea.Y;
+}

src/modules/cmdpal/Microsoft.CmdPal.UI/MainWindow.xaml.cs

@@ -21,7 +21,6 @@ using Microsoft.CmdPal.UI.ViewModels.Messages;
 using Microsoft.CmdPal.UI.ViewModels.Services;
 using Microsoft.Extensions.DependencyInjection;
 using Microsoft.PowerToys.Telemetry;
-using Microsoft.UI;
 using Microsoft.UI.Composition;
 using Microsoft.UI.Composition.SystemBackdrops;
 using Microsoft.UI.Input;
@@ -32,13 +31,9 @@ using Windows.ApplicationModel.Activation;
 using Windows.Foundation;
 using Windows.Graphics;
 using Windows.System;
-using Windows.UI;
-using Windows.UI.WindowManagement;
 using Windows.Win32;
 using Windows.Win32.Foundation;
 using Windows.Win32.Graphics.Dwm;
-using Windows.Win32.Graphics.Gdi;
-using Windows.Win32.UI.HiDpi;
 using Windows.Win32.UI.Input.KeyboardAndMouse;
 using Windows.Win32.UI.WindowsAndMessaging;
 using WinRT;
@@ -60,9 +55,6 @@ public sealed partial class MainWindow : WindowEx,
     IRecipient<DragCompletedMessage>,
     IDisposable
 {
-    private const int DefaultWidth = 800;
-    private const int DefaultHeight = 480;
-
     [System.Diagnostics.CodeAnalysis.SuppressMessage("StyleCop.CSharp.NamingRules", "SA1310:Field names should not contain underscore", Justification = "Stylistically, window messages are WM_")]
     [System.Diagnostics.CodeAnalysis.SuppressMessage("StyleCop.CSharp.NamingRules", "SA1306:Field names should begin with lower-case letter", Justification = "Stylistically, window messages are WM_")]
     private readonly uint WM_TASKBAR_RESTART;
@@ -226,39 +218,40 @@ public sealed partial class MainWindow : WindowEx,
         PositionCentered(displayArea);
     }
 
+    private void PositionCentered(DisplayArea displayArea)
+    {
+        var position = WindowPositionHelper.CalculateCenteredPosition(
+            displayArea,
+            AppWindow.Size,
+            (int)this.GetDpiForWindow());
+
+        if (position is not null)
+        {
+            // Use Move(), not MoveAndResize(). Windows auto-resizes on DPI change via WM_DPICHANGED;
+            // the helper already accounts for this when calculating the centered position.
+            AppWindow.Move((PointInt32)position);
+        }
+    }
+
     private void RestoreWindowPosition()
     {
         var settings = App.Current.Services.GetService<SettingsModel>();
-        if (settings?.LastWindowPosition is not WindowPosition savedPosition)
+        if (settings?.LastWindowPosition is not { Width: > 0, Height: > 0 } savedPosition)
         {
             PositionCentered();
             return;
         }
 
-        if (savedPosition.Width <= 0 || savedPosition.Height <= 0)
-        {
-            PositionCentered();
-            return;
-        }
+        // MoveAndResize is safe here—we're restoring a saved state at startup,
+        // not moving a live window between displays.
+        var newRect = WindowPositionHelper.AdjustRectForVisibility(
+            savedPosition.ToPhysicalWindowRectangle(),
+            new SizeInt32(savedPosition.ScreenWidth, savedPosition.ScreenHeight),
+            savedPosition.Dpi);
 
-        var newRect = EnsureWindowIsVisible(savedPosition.ToPhysicalWindowRectangle(), new SizeInt32(savedPosition.ScreenWidth, savedPosition.ScreenHeight), savedPosition.Dpi);
         AppWindow.MoveAndResize(newRect);
     }
 
-    private void PositionCentered(DisplayArea displayArea)
-    {
-        if (displayArea is not null)
-        {
-            var centeredPosition = AppWindow.Position;
-            centeredPosition.X = (displayArea.WorkArea.Width - AppWindow.Size.Width) / 2;
-            centeredPosition.Y = (displayArea.WorkArea.Height - AppWindow.Size.Height) / 2;
-
-            centeredPosition.X += displayArea.WorkArea.X;
-            centeredPosition.Y += displayArea.WorkArea.Y;
-            AppWindow.Move(centeredPosition);
-        }
-    }
-
     private void UpdateWindowPositionInMemory()
     {
         var displayArea = DisplayArea.GetFromWindowId(AppWindow.Id, DisplayAreaFallback.Nearest) ?? DisplayArea.Primary;
@@ -352,7 +345,8 @@ public sealed partial class MainWindow : WindowEx,
 
         if (target == MonitorBehavior.ToLast)
         {
-            var newRect = EnsureWindowIsVisible(_currentWindowPosition.ToPhysicalWindowRectangle(), new SizeInt32(_currentWindowPosition.ScreenWidth, _currentWindowPosition.ScreenHeight), _currentWindowPosition.Dpi);
+            var originalScreen = new SizeInt32(_currentWindowPosition.ScreenWidth, _currentWindowPosition.ScreenHeight);
+            var newRect = WindowPositionHelper.AdjustRectForVisibility(_currentWindowPosition.ToPhysicalWindowRectangle(), originalScreen, _currentWindowPosition.Dpi);
             AppWindow.MoveAndResize(newRect);
         }
         else
@@ -382,115 +376,7 @@ public sealed partial class MainWindow : WindowEx,
         PInvoke.SetWindowPos(hwnd, HWND.HWND_TOPMOST, 0, 0, 0, 0, SET_WINDOW_POS_FLAGS.SWP_NOMOVE | SET_WINDOW_POS_FLAGS.SWP_NOSIZE);
     }
 
-    /// <summary>
-    /// Ensures that the window rectangle is visible on-screen.
-    /// </summary>
-    /// <param name="windowRect">The window rectangle in physical pixels.</param>
-    /// <param name="originalScreen">The desktop area the window was positioned on.</param>
-    /// <param name="originalDpi">The window's original DPI.</param>
-    /// <returns>
-    /// A window rectangle in physical pixels, moved to the nearest display and resized
-    /// if the DPI has changed.
-    /// </returns>
-    private static RectInt32 EnsureWindowIsVisible(RectInt32 windowRect, SizeInt32 originalScreen, int originalDpi)
-    {
-        var displayArea = DisplayArea.GetFromRect(windowRect, DisplayAreaFallback.Nearest);
-        if (displayArea is null)
-        {
-            return windowRect;
-        }
-
-        var workArea = displayArea.WorkArea;
-        if (workArea.Width <= 0 || workArea.Height <= 0)
-        {
-            // Fallback, nothing reasonable to do
-            return windowRect;
-        }
-
-        var effectiveDpi = GetEffectiveDpiFromDisplayId(displayArea);
-        if (originalDpi <= 0)
-        {
-            originalDpi = effectiveDpi; // use current DPI as baseline (no scaling adjustment needed)
-        }
-
-        var hasInvalidSize = windowRect.Width <= 0 || windowRect.Height <= 0;
-        if (hasInvalidSize)
-        {
-            windowRect = new RectInt32(windowRect.X, windowRect.Y, DefaultWidth, DefaultHeight);
-        }
-
-        // If we have a DPI change, scale the window rectangle accordingly
-        if (effectiveDpi != originalDpi)
-        {
-            var scalingFactor = effectiveDpi / (double)originalDpi;
-            windowRect = new RectInt32(
-                (int)Math.Round(windowRect.X * scalingFactor),
-                (int)Math.Round(windowRect.Y * scalingFactor),
-                (int)Math.Round(windowRect.Width * scalingFactor),
-                (int)Math.Round(windowRect.Height * scalingFactor));
-        }
-
-        var targetWidth = Math.Min(windowRect.Width, workArea.Width);
-        var targetHeight = Math.Min(windowRect.Height, workArea.Height);
-
-        // Ensure at least some minimum visible area (e.g., 100 pixels)
-        // This helps prevent the window from being entirely offscreen, regardless of display scaling.
-        const int minimumVisibleSize = 100;
-        var isOffscreen =
-            windowRect.X + minimumVisibleSize > workArea.X + workArea.Width ||
-            windowRect.X + windowRect.Width - minimumVisibleSize < workArea.X ||
-            windowRect.Y + minimumVisibleSize > workArea.Y + workArea.Height ||
-            windowRect.Y + windowRect.Height - minimumVisibleSize < workArea.Y;
-
-        // if the work area size has changed, re-center the window
-        var workAreaSizeChanged =
-            originalScreen.Width != workArea.Width ||
-            originalScreen.Height != workArea.Height;
-
-        int targetX;
-        int targetY;
-        var recenter = isOffscreen || workAreaSizeChanged || hasInvalidSize;
-        if (recenter)
-        {
-            targetX = workArea.X + ((workArea.Width - targetWidth) / 2);
-            targetY = workArea.Y + ((workArea.Height - targetHeight) / 2);
-        }
-        else
-        {
-            targetX = windowRect.X;
-            targetY = windowRect.Y;
-        }
-
-        return new RectInt32(targetX, targetY, targetWidth, targetHeight);
-    }
-
-    private static int GetEffectiveDpiFromDisplayId(DisplayArea displayArea)
-    {
-        var effectiveDpi = 96;
-
-        var hMonitor = (HMONITOR)Win32Interop.GetMonitorFromDisplayId(displayArea.DisplayId);
-        if (!hMonitor.IsNull)
-        {
-            var hr = PInvoke.GetDpiForMonitor(hMonitor, MONITOR_DPI_TYPE.MDT_EFFECTIVE_DPI, out var dpiX, out _);
-            if (hr == 0)
-            {
-                effectiveDpi = (int)dpiX;
-            }
-            else
-            {
-                Logger.LogWarning($"GetDpiForMonitor failed with HRESULT: 0x{hr.Value:X8} on display {displayArea.DisplayId}");
-            }
-        }
-
-        if (effectiveDpi <= 0)
-        {
-            effectiveDpi = 96;
-        }
-
-        return effectiveDpi;
-    }
-
-    private DisplayArea GetScreen(HWND currentHwnd, MonitorBehavior target)
+    private static DisplayArea GetScreen(HWND currentHwnd, MonitorBehavior target)
     {
         // Leaving a note here, in case we ever need it:
         // https://github.com/microsoft/microsoft-ui-xaml/issues/6454

src/modules/cmdpal/Microsoft.CmdPal.UI/Microsoft.CmdPal.UI.csproj

@@ -83,6 +83,7 @@
     <None Remove="Pages\Settings\GeneralPage.xaml" />
     <None Remove="SettingsWindow.xaml" />
     <None Remove="Settings\AppearancePage.xaml" />
+    <None Remove="Settings\InternalPage.xaml" />
     <None Remove="ShellPage.xaml" />
     <None Remove="Styles\Colors.xaml" />
     <None Remove="Styles\Settings.xaml" />
@@ -264,6 +265,11 @@
       <Generator>MSBuild:Compile</Generator>
     </Page>
   </ItemGroup>
+  <ItemGroup>
+    <Page Update="Settings\InternalPage.xaml">
+      <Generator>MSBuild:Compile</Generator>
+    </Page>
+  </ItemGroup>
   <ItemGroup>
     <Page Update="Styles\Colors.xaml">
       <Generator>MSBuild:Compile</Generator>

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

@@ -257,11 +257,11 @@ public sealed partial class ShellPage : Microsoft.UI.Xaml.Controls.Page,
     {
         _ = DispatcherQueue.TryEnqueue(() =>
         {
-            OpenSettings();
+            OpenSettings(message.SettingsPageTag);
         });
     }
 
-    public void OpenSettings()
+    public void OpenSettings(string pageTag)
     {
         if (_settingsWindow is null)
         {
@@ -270,6 +270,7 @@ public sealed partial class ShellPage : Microsoft.UI.Xaml.Controls.Page,
 
         _settingsWindow.Activate();
         _settingsWindow.BringToFront();
+        _settingsWindow.Navigate(pageTag);
     }
 
     public void Receive(ShowDetailsMessage message)

src/modules/cmdpal/Microsoft.CmdPal.UI/Settings/ExtensionsPage.xaml

@@ -229,12 +229,26 @@
                                     <controls:SettingsCard.HeaderIcon>
                                         <cpcontrols:ContentIcon>
                                             <cpcontrols:ContentIcon.Content>
-                                                <cpcontrols:IconBox
-                                                    Width="20"
-                                                    Height="20"
+                                                <controls:SwitchPresenter
                                                     AutomationProperties.AccessibilityView="Raw"
-                                                    SourceKey="{x:Bind Icon, Mode=OneWay}"
-                                                    SourceRequested="{x:Bind helpers:IconCacheProvider.SourceRequested}" />
+                                                    TargetType="x:Boolean"
+                                                    Value="{x:Bind Icon.IsSet, FallbackValue=x:False, Mode=OneWay}">
+                                                    <controls:Case Value="True">
+                                                        <cpcontrols:IconBox
+                                                            Width="20"
+                                                            Height="20"
+                                                            AutomationProperties.AccessibilityView="Raw"
+                                                            SourceKey="{x:Bind Icon, Mode=OneWay}"
+                                                            SourceRequested="{x:Bind helpers:IconCacheProvider.SourceRequested}" />
+                                                    </controls:Case>
+                                                    <controls:Case Value="False">
+                                                        <Image
+                                                            Width="20"
+                                                            Height="20"
+                                                            AutomationProperties.AccessibilityView="Raw"
+                                                            Source="ms-appx:///Assets/Icons/ExtensionIconPlaceholder.png" />
+                                                    </controls:Case>
+                                                </controls:SwitchPresenter>
                                             </cpcontrols:ContentIcon.Content>
                                         </cpcontrols:ContentIcon>
                                     </controls:SettingsCard.HeaderIcon>

src/modules/cmdpal/Microsoft.CmdPal.UI/Settings/InternalPage.SampleData.cs

@@ -0,0 +1,45 @@
+// Copyright (c) Microsoft Corporation
+// The Microsoft Corporation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+namespace Microsoft.CmdPal.UI.Settings;
+
+public partial class InternalPage
+{
+    internal static class SampleData
+    {
+        internal static string ExceptionMessageWithPii { get; } =
+            $"""
+             Test exception with personal information; thrown from the UI thread
+
+             Here is e-mail address <jane.doe@contoso.com>
+             IPv4 address: 192.168.100.1
+             IPv4 loopback address: 127.0.0.1
+             MAC address: 00-14-22-01-23-45
+             IPv6 address: 2001:0db8:85a3:0000:0000:8a2e:0370:7334
+             IPv6 loopback address: ::1
+             Password: P@ssw0rd123!
+             Password=secret
+             Api key: 1234567890abcdef
+             PostgreSQL connection string: Host=localhost;Username=postgres;Password=secret;Database=mydb
+             InstrumentationKey=00000000-0000-0000-0000-000000000000;EndpointSuffix=ai.contoso.com;
+             X-API-key: 1234567890abcdef
+             Pet-Shop-Subscription-Key: 1234567890abcdef
+             Here is a user name {Environment.UserName}
+             And here is a profile path {Environment.GetFolderPath(Environment.SpecialFolder.UserProfile)}\Pictures
+             Here is a local app data path {Environment.GetFolderPath(Environment.SpecialFolder.LocalApplicationData)}\Microsoft\PowerToys\CmdPal
+             Here is machine name {Environment.MachineName}
+             JWT token: eyJhbGciOiJIUzI1NiIsInR5cCI6IkpXVCJ9.eyJzdWIiOiIxMjM0NTY3ODkwIiwibmFtZSI6IkpvaG4gRG9lIiwiYWRtaW4iOnRydWUsImlhdCI6MTUxNjIzOTAyMn0.KMUFsIDTnFmyG3nMiGM6H9FNFUROf3wh7SmqJp-QV30
+             User email john.doe@company.com failed validation
+             File not found: {Environment.GetFolderPath(Environment.SpecialFolder.MyDocuments)}\\secret.txt
+             Connection string: Server=localhost;User ID=admin;Password=secret123;Database=test
+             Phone number 555-123-4567 is invalid
+             API key abc123def456ghi789jkl012mno345pqr678 expired
+             Failed to connect to https://api.internal-company.com/users/12345?token=secret_abc123
+             Error accessing file://C:/Users/john.doe/Documents/confidential.pdf
+             JDBC connection failed: jdbc://database-server:5432/userdb?user=admin&password=secret
+             FTP upload error: ftp://internal-server.company.com/uploads/user_data.csv
+             Email service error: mailto:admin@internal-company.com?subject=Alert
+             """;
+    }
+}

src/modules/cmdpal/Microsoft.CmdPal.UI/Settings/InternalPage.xaml

@@ -0,0 +1,75 @@
+<?xml version="1.0" encoding="utf-8" ?>
+<Page
+    x:Class="Microsoft.CmdPal.UI.Settings.InternalPage"
+    xmlns="http://schemas.microsoft.com/winfx/2006/xaml/presentation"
+    xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
+    xmlns:controls="using:CommunityToolkit.WinUI.Controls"
+    xmlns:d="http://schemas.microsoft.com/expression/blend/2008"
+    xmlns:mc="http://schemas.openxmlformats.org/markup-compatibility/2006"
+    xmlns:ui="using:CommunityToolkit.WinUI"
+    mc:Ignorable="d">
+
+    <Grid>
+        <Grid.RowDefinitions>
+            <RowDefinition Height="Auto" />
+            <RowDefinition Height="*" />
+        </Grid.RowDefinitions>
+        <ScrollViewer Grid.Row="1">
+            <Grid Padding="16">
+                <StackPanel
+                    MaxWidth="1000"
+                    HorizontalAlignment="Stretch"
+                    Spacing="{StaticResource SettingsCardSpacing}">
+
+                    <TextBlock Style="{StaticResource BodyTextBlockStyle}" Text="Tools on this page are for internal use only. This page is not visible in CI builds." />
+
+                    <!--  Exception Handling Section  -->
+                    <TextBlock Style="{StaticResource SettingsSectionHeaderTextBlockStyle}" Text="Exception Handling" />
+                    <controls:SettingsExpander
+                        Description="Actions for testing global exception handling from the application"
+                        Header="Throw exceptions"
+                        HeaderIcon="{ui:FontIcon Glyph=&#xE783;}"
+                        IsExpanded="True">
+                        <controls:SettingsExpander.Items>
+                            <controls:SettingsCard Header="Throw an unhandled exception from the UI thread">
+                                <Button Click="ThrowPlainMainThreadException_Click" Content="Throw" />
+                            </controls:SettingsCard>
+                            <controls:SettingsCard Header="Throw an unhandled exception from the UI thread (with PII)">
+                                <Button Click="ThrowPlainMainThreadExceptionPii_Click" Content="Throw" />
+                            </controls:SettingsCard>
+                            <controls:SettingsCard Description="Throw with delay, when the task is collected by the GC" Header="Throw unobserved exception from a task">
+                                <Button Click="ThrowExceptionInUnobservedTask_Click" Content="Throw" />
+                            </controls:SettingsCard>
+                        </controls:SettingsExpander.Items>
+                    </controls:SettingsExpander>
+
+                    <!--  Diagnostics Section  -->
+                    <TextBlock Style="{StaticResource SettingsSectionHeaderTextBlockStyle}" Text="Diagnostics" />
+                    <controls:SettingsCard
+                        x:Name="LogsSettingsCard"
+                        Header="Logs folder"
+                        HeaderIcon="{ui:FontIcon Glyph=&#xE8B7;}">
+                        <Button Click="OpenLogsCardClicked" Content="Open folder" />
+                    </controls:SettingsCard>
+                    <controls:SettingsCard
+                        x:Name="CurrentLogFileSettingsCard"
+                        Header="Current log file"
+                        HeaderIcon="{ui:FontIcon Glyph=&#xF7BB;}">
+                        <Button Click="OpenCurrentLogCardClicked" Content="Open log" />
+                    </controls:SettingsCard>
+
+                    <!--  Data Section  -->
+                    <TextBlock Style="{StaticResource SettingsSectionHeaderTextBlockStyle}" Text="Data and Files" />
+                    <controls:SettingsCard
+                        x:Name="ConfigurationFolderSettingsCard"
+                        Header="Configuration folder"
+                        HeaderIcon="{ui:FontIcon Glyph=&#xF73D;}">
+                        <Button Click="OpenConfigFolderCardClick" Content="Open folder" />
+                    </controls:SettingsCard>
+
+
+                </StackPanel>
+            </Grid>
+        </ScrollViewer>
+    </Grid>
+</Page>

src/modules/cmdpal/Microsoft.CmdPal.UI/Settings/InternalPage.xaml.cs

@@ -0,0 +1,92 @@
+// 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 ManagedCommon;
+using Microsoft.CommandPalette.Extensions.Toolkit;
+using Microsoft.UI.Xaml;
+using Windows.System;
+using Page = Microsoft.UI.Xaml.Controls.Page;
+
+namespace Microsoft.CmdPal.UI.Settings;
+
+/// <summary>
+/// An empty page that can be used on its own or navigated to within a Frame.
+/// </summary>
+public sealed partial class InternalPage : Page
+{
+    public InternalPage()
+    {
+        InitializeComponent();
+    }
+
+    private void ThrowPlainMainThreadException_Click(object sender, RoutedEventArgs e)
+    {
+        Logger.LogDebug("Throwing test exception from the UI thread");
+        throw new NotImplementedException("Test exception; thrown from the UI thread");
+    }
+
+    private void ThrowExceptionInUnobservedTask_Click(object sender, RoutedEventArgs e)
+    {
+        Logger.LogDebug("Starting a task that will throw test exception");
+        Task.Run(() =>
+        {
+            Logger.LogDebug("Throwing test exception from a task");
+            throw new InvalidOperationException("Test exception; thrown from a task");
+        });
+    }
+
+    private void ThrowPlainMainThreadExceptionPii_Click(object sender, RoutedEventArgs e)
+    {
+        Logger.LogDebug("Throwing test exception from the UI thread (PII)");
+        throw new InvalidOperationException(SampleData.ExceptionMessageWithPii);
+    }
+
+    private async void OpenLogsCardClicked(object sender, RoutedEventArgs e)
+    {
+        try
+        {
+            var logFolderPath = Logger.CurrentVersionLogDirectoryPath;
+            if (Directory.Exists(logFolderPath))
+            {
+                await Launcher.LaunchFolderPathAsync(logFolderPath);
+            }
+        }
+        catch (Exception ex)
+        {
+            Logger.LogError("Failed to open directory in Explorer", ex);
+        }
+    }
+
+    private async void OpenCurrentLogCardClicked(object sender, RoutedEventArgs e)
+    {
+        try
+        {
+            var logPath = Logger.CurrentLogFile;
+            if (File.Exists(logPath))
+            {
+                await Launcher.LaunchUriAsync(new Uri(logPath));
+            }
+        }
+        catch (Exception ex)
+        {
+            Logger.LogError("Failed to open log file", ex);
+        }
+    }
+
+    private async void OpenConfigFolderCardClick(object sender, RoutedEventArgs e)
+    {
+        try
+        {
+            var directory = Utilities.BaseSettingsPath("Microsoft.CmdPal");
+            if (Directory.Exists(directory))
+            {
+                await Launcher.LaunchFolderPathAsync(directory);
+            }
+        }
+        catch (Exception ex)
+        {
+            Logger.LogError("Failed to open directory in Explorer", ex);
+        }
+    }
+}

src/modules/cmdpal/Microsoft.CmdPal.UI/Settings/SettingsWindow.xaml

@@ -72,6 +72,7 @@
                     x:Uid="Settings_GeneralPage_NavigationViewItem_Extensions"
                     Icon="{ui:FontIcon Glyph=}"
                     Tag="Extensions" />
+                <!--  "Internal Tools" page item is added dynamically from code  -->
             </NavigationView.MenuItems>
             <Grid>
                 <Grid.RowDefinitions>

src/modules/cmdpal/Microsoft.CmdPal.UI/Settings/SettingsWindow.xaml.cs

@@ -30,6 +30,8 @@ public sealed partial class SettingsWindow : WindowEx,
 {
     private readonly LocalKeyboardListener _localKeyboardListener;
 
+    private readonly NavigationViewItem? _internalNavItem;
+
     public ObservableCollection<Crumb> BreadCrumbs { get; } = [];
 
     // Gets or sets optional action invoked after NavigationView is loaded.
@@ -54,6 +56,23 @@ public sealed partial class SettingsWindow : WindowEx,
         _localKeyboardListener.Start();
         Closed += SettingsWindow_Closed;
         RootElement.AddHandler(UIElement.PointerPressedEvent, new PointerEventHandler(RootElement_OnPointerPressed), true);
+
+        if (!BuildInfo.IsCiBuild)
+        {
+            _internalNavItem = new NavigationViewItem
+            {
+                Content = "Internal Tools",
+                Icon = new FontIcon { Glyph = "\uEC7A" },
+                Tag = "Internal",
+            };
+            NavView.MenuItems.Add(_internalNavItem);
+        }
+        else
+        {
+            _internalNavItem = null;
+        }
+
+        Navigate("General");
     }
 
     private void SettingsWindow_Closed(object sender, WindowEventArgs args)
@@ -68,9 +87,6 @@ public sealed partial class SettingsWindow : WindowEx,
         // Delay necessary to ensure NavigationView visual state can match navigation
         Task.Delay(500).ContinueWith(_ => this.NavigationViewLoaded?.Invoke(), TaskScheduler.FromCurrentSynchronizationContext());
 
-        NavView.SelectedItem = NavView.MenuItems[0];
-        Navigate("General");
-
         if (sender is NavigationView navigationView)
         {
             // Register for pane open/close changes to announce to screen readers
@@ -96,15 +112,33 @@ public sealed partial class SettingsWindow : WindowEx,
         Navigate((selectedItem.Tag as string)!);
     }
 
-    private void Navigate(string page)
+    internal void Navigate(string page)
     {
-        var pageType = page switch
+        Type? pageType;
+        switch (page)
         {
-            "General" => typeof(GeneralPage),
-            "Appearance" => typeof(AppearancePage),
-            "Extensions" => typeof(ExtensionsPage),
-            _ => null,
-        };
+            case "General":
+                pageType = typeof(GeneralPage);
+                break;
+            case "Appearance":
+                pageType = typeof(AppearancePage);
+                break;
+            case "Extensions":
+                pageType = typeof(ExtensionsPage);
+                break;
+            case "Internal":
+                pageType = typeof(InternalPage);
+                break;
+            case "":
+                // intentional no-op: empty tag means no navigation
+                pageType = null;
+                break;
+            default:
+                // unknown page, no-op and log
+                pageType = null;
+                Logger.LogError($"Unknown settings page tag '{page}'");
+                break;
+        }
 
         if (pageType is not null)
         {
@@ -268,6 +302,12 @@ public sealed partial class SettingsWindow : WindowEx,
             BreadCrumbs.Add(new(extensionsPageType, extensionsPageType));
             BreadCrumbs.Add(new(vm.DisplayName, vm));
         }
+        else if (e.SourcePageType == typeof(InternalPage) && _internalNavItem is not null)
+        {
+            NavView.SelectedItem = _internalNavItem;
+            var pageType = "Internal";
+            BreadCrumbs.Add(new(pageType, pageType));
+        }
         else
         {
             BreadCrumbs.Add(new($"[{e.SourcePageType?.Name}]", string.Empty));

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

@@ -8,8 +8,10 @@ using System.Globalization;
 using System.Text.RegularExpressions;
 using CommunityToolkit.Mvvm.ComponentModel;
 using CommunityToolkit.Mvvm.Input;
+using CommunityToolkit.Mvvm.Messaging;
 using ManagedCommon;
 using Microsoft.CmdPal.UI.Helpers;
+using Microsoft.CmdPal.UI.Messages;
 using Microsoft.UI;
 using Windows.System;
 using Windows.UI;
@@ -99,6 +101,12 @@ internal sealed partial class DevRibbonViewModel : ObservableObject
         LatestLogs.Clear();
     }
 
+    [RelayCommand]
+    private void OpenInternalTools()
+    {
+        WeakReferenceMessenger.Default.Send(new OpenSettingsMessage("Internal"));
+    }
+
     private sealed partial class DevRibbonTraceListener(DevRibbonViewModel viewModel) : TraceListener
     {
         private const string TimestampFormat = "yyyy-MM-dd HH:mm:ss.fff";

src/modules/cmdpal/Tests/Microsoft.CmdPal.Core.Common.UnitTests/GlobalUsings.cs

@@ -0,0 +1,9 @@
+// Copyright (c) Microsoft Corporation
+// The Microsoft Corporation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+global using System;
+global using System.Collections.Generic;
+global using System.Diagnostics.CodeAnalysis;
+global using System.Linq;
+global using Microsoft.VisualStudio.TestTools.UnitTesting;

src/modules/cmdpal/Tests/Microsoft.CmdPal.Core.Common.UnitTests/Microsoft.CmdPal.Core.Common.UnitTests.csproj

@@ -0,0 +1,25 @@
+<Project Sdk="Microsoft.NET.Sdk">
+  <!-- Look at Directory.Build.props in root for common stuff as well -->
+  <Import Project="..\..\..\..\Common.Dotnet.CsWinRT.props" />
+
+  <PropertyGroup>
+    <IsPackable>false</IsPackable>
+    <IsTestProject>true</IsTestProject>
+    <RootNamespace>Microsoft.CmdPal.Common.UnitTests</RootNamespace>
+    <OutputPath>$(SolutionDir)$(Platform)\$(Configuration)\WinUI3Apps\CmdPal\tests\</OutputPath>
+    <AppendTargetFrameworkToOutputPath>false</AppendTargetFrameworkToOutputPath>
+    <AppendRuntimeIdentifierToOutputPath>false</AppendRuntimeIdentifierToOutputPath>
+    <Nullable>enable</Nullable>
+    <LangVersion>preview</LangVersion>
+  </PropertyGroup>
+
+  <ItemGroup>
+    <PackageReference Include="Moq" />
+    <PackageReference Include="MSTest" />
+  </ItemGroup>
+
+  <ItemGroup>
+    <ProjectReference Include="..\..\Core\Microsoft.CmdPal.Core.Common\Microsoft.CmdPal.Core.Common.csproj" />
+    <ProjectReference Include="..\Microsoft.CmdPal.Ext.UnitTestsBase\Microsoft.CmdPal.Ext.UnitTestBase.csproj" />
+  </ItemGroup>
+</Project>

src/modules/cmdpal/Tests/Microsoft.CmdPal.Core.Common.UnitTests/Services/Sanitizer/ConnectionStringRuleProviderTests.cs

@@ -0,0 +1,107 @@
+// 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.UnitTests.TestUtils;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Common.UnitTests.Services.Sanitizer;
+
+[TestClass]
+public class ConnectionStringRuleProviderTests
+{
+    [TestMethod]
+    public void GetRules_ShouldReturnExpectedRules()
+    {
+        // Arrange
+        var provider = new ConnectionStringRuleProvider();
+
+        // Act
+        var rules = provider.GetRules();
+
+        // Assert
+        var ruleList = new List<SanitizationRule>(rules);
+        Assert.AreEqual(1, ruleList.Count);
+        Assert.AreEqual("Connection string parameters", ruleList[0].Description);
+    }
+
+    [DataTestMethod]
+    [DataRow("Server=localhost;Database=mydb;User ID=admin;Password=secret123", "Server=[REDACTED];Database=[REDACTED];User ID=[REDACTED];Password=[REDACTED]")]
+    [DataRow("Data Source=server.example.com;Initial Catalog=testdb;Uid=user;Pwd=pass", "Data Source=[REDACTED];Initial Catalog=[REDACTED];Uid=[REDACTED];Pwd=[REDACTED]")]
+    [DataRow("Server=localhost;Password=my_secret", "Server=[REDACTED];Password=[REDACTED]")]
+    [DataRow("No connection string here", "No connection string here")]
+    public void ConnectionStringRules_ShouldMaskConnectionStringParameters(string input, string expected)
+    {
+        // Arrange
+        var provider = new ConnectionStringRuleProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("Password=\"complexPassword123!\"", "Password=[REDACTED]")]
+    [DataRow("Password='myPassword'", "Password=[REDACTED]")]
+    [DataRow("Password=unquotedSecret", "Password=[REDACTED]")]
+    public void ConnectionStringRules_ShouldHandleQuotedAndUnquotedValues(string input, string expected)
+    {
+        // Arrange
+        var provider = new ConnectionStringRuleProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("SERVER=server1;PASSWORD=pass1", "SERVER=[REDACTED];PASSWORD=[REDACTED]")]
+    [DataRow("server=server1;password=pass1", "server=[REDACTED];password=[REDACTED]")]
+    [DataRow("Server=server1;Password=pass1", "Server=[REDACTED];Password=[REDACTED]")]
+    public void ConnectionStringRules_ShouldBeCaseInsensitive(string input, string expected)
+    {
+        // Arrange
+        var provider = new ConnectionStringRuleProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("User ID=admin;Username=john;Password=secret", "User ID=[REDACTED];Username=[REDACTED];Password=[REDACTED]")]
+    [DataRow("Database=mydb;Uid=user1;Pwd=pass1;Server=localhost", "Database=[REDACTED];Uid=[REDACTED];Pwd=[REDACTED];Server=[REDACTED]")]
+    public void ConnectionStringRules_ShouldHandleMultipleParameters(string input, string expected)
+    {
+        // Arrange
+        var provider = new ConnectionStringRuleProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("Server = localhost ; Password = secret123", "Server=[REDACTED] ; Password=[REDACTED]")]
+    [DataRow("Initial Catalog=db;  User ID=admin;  Password=pass", "Initial Catalog=[REDACTED];  User ID=[REDACTED];  Password=[REDACTED]")]
+    public void ConnectionStringRules_ShouldHandleWhitespace(string input, string expected)
+    {
+        // Arrange
+        var provider = new ConnectionStringRuleProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+}

src/modules/cmdpal/Tests/Microsoft.CmdPal.Core.Common.UnitTests/Services/Sanitizer/ErrorReportSanitizerTests.TestData.cs

@@ -0,0 +1,81 @@
+// 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.Common.UnitTests.Services.Sanitizer;
+
+public partial class ErrorReportSanitizerTests
+{
+    private static class TestData
+    {
+        internal static string Input =>
+             $"""
+              HRESULT: 0x80004005
+              HRESULT: -2147467259
+
+              Here is e-mail address <jane.doe@contoso.com>
+              IPv4 address: 192.168.100.1
+              IPv4 loopback address: 127.0.0.1
+              MAC address: 00-14-22-01-23-45
+              IPv6 address: 2001:0db8:85a3:0000:0000:8a2e:0370:7334
+              IPv6 loopback address: ::1
+              Password: P@ssw0rd123!
+              Password=secret
+              Api key: 1234567890abcdef
+              PostgreSQL connection string: Host=localhost;Username=postgres;Password=secret;Database=mydb
+              InstrumentationKey=00000000-0000-0000-0000-000000000000;EndpointSuffix=ai.contoso.com;
+              X-API-key: 1234567890abcdef
+              Pet-Shop-Subscription-Key: 1234567890abcdef
+              Here is a user name {Environment.UserName}
+              And here is a profile path {Environment.GetFolderPath(Environment.SpecialFolder.UserProfile)}\RandomFolder
+              Here is a local app data path {Environment.GetFolderPath(Environment.SpecialFolder.LocalApplicationData)}\Microsoft\PowerToys\CmdPal
+              Here is machine name {Environment.MachineName}
+              JWT token: eyJhbGciOiJIUzI1NiIsInR5cCI6IkpXVCJ9.eyJzdWIiOiIxMjM0NTY3ODkwIiwibmFtZSI6IkpvaG4gRG9lIiwiYWRtaW4iOnRydWUsImlhdCI6MTUxNjIzOTAyMn0.KMUFsIDTnFmyG3nMiGM6H9FNFUROf3wh7SmqJp-QV30
+              User email john.doe@company.com failed validation
+              File not found: {Environment.GetFolderPath(Environment.SpecialFolder.MyDocuments)}\\secret.txt
+              Connection string: Server=localhost;User ID=admin;Password=secret123;Database=test
+              Phone number 555-123-4567 is invalid
+              API key abc123def456ghi789jkl012mno345pqr678 expired
+              Failed to connect to https://api.internal-company.com/users/12345?token=secret_abc123
+              Error accessing file://C:/Users/john.doe/Documents/confidential.pdf
+              JDBC connection failed: jdbc://database-server:5432/userdb?user=admin&password=secret
+              FTP upload error: ftp://internal-server.company.com/uploads/user_data.csv
+              Email service error: mailto:admin@internal-company.com?subject=Alert
+              """;
+
+        public const string Expected =
+            $"""
+             HRESULT: 0x80004005
+             HRESULT: -2147467259
+
+             Here is e-mail address <[EMAIL_REDACTED]>
+             IPv4 address: [IP4_REDACTED]
+             IPv4 loopback address: [IP4_REDACTED]
+             MAC address: [MAC_ADDRESS_REDACTED]
+             IPv6 address: [IP6_REDACTED]
+             IPv6 loopback address: [IP6_REDACTED]
+             Password: [REDACTED]
+             Password= [REDACTED]
+             Api key: [REDACTED]
+             PostgreSQL connection string: [REDACTED]
+             InstrumentationKey= [REDACTED]
+             X-API-key: [REDACTED]
+             Pet-Shop-Subscription-Key: [REDACTED]
+             Here is a user name [USERNAME_REDACTED]
+             And here is a profile path [USER_PROFILE_DIR]RandomFolder
+             Here is a local app data path [LOCALAPPLICATIONDATA_DIR]Microsoft\PowerToys\CmdPal
+             Here is machine name [MACHINE_NAME_REDACTED]
+             JWT token: [REDACTED]
+             User email [EMAIL_REDACTED] failed validation
+             File not found: [MYDOCUMENTS_DIR]se****.txt
+             Connection string: [REDACTED] ID=[REDACTED];Password= [REDACTED]
+             Phone number [PHONE_REDACTED] is invalid
+             API key [TOKEN_REDACTED] expired
+             Failed to connect to [URL_REDACTED]
+             Error accessing [URL_REDACTED]
+             JDBC connection failed: [URL_REDACTED]
+             FTP upload error: [URL_REDACTED]
+             Email service error: mailto:[EMAIL_REDACTED]?subject=Alert
+             """;
+    }
+}

src/modules/cmdpal/Tests/Microsoft.CmdPal.Core.Common.UnitTests/Services/Sanitizer/ErrorReportSanitizerTests.cs

@@ -0,0 +1,25 @@
+// Copyright (c) Microsoft Corporation
+// The Microsoft Corporation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+
+namespace Microsoft.CmdPal.Common.UnitTests.Services.Sanitizer;
+
+[TestClass]
+public partial class ErrorReportSanitizerTests
+{
+    [TestMethod]
+    public void Sanitize_ShouldMaskPiiInErrorReport()
+    {
+        // Arrange
+        var reportSanitizer = new ErrorReportSanitizer();
+        var input = TestData.Input;
+
+        // Act
+        var result = reportSanitizer.Sanitize(input);
+
+        // Assert
+        Assert.AreEqual(TestData.Expected, result);
+    }
+}

src/modules/cmdpal/Tests/Microsoft.CmdPal.Core.Common.UnitTests/Services/Sanitizer/PiiRuleProviderTests.cs

@@ -0,0 +1,122 @@
+// 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.UnitTests.TestUtils;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Common.UnitTests.Services.Sanitizer;
+
+[TestClass]
+public class PiiRuleProviderTests
+{
+    [TestMethod]
+    public void GetRules_ShouldReturnExpectedRules()
+    {
+        // Arrange
+        var provider = new PiiRuleProvider();
+
+        // Act
+        var rules = provider.GetRules();
+
+        // Assert
+        var ruleList = new List<SanitizationRule>(rules);
+        Assert.AreEqual(4, ruleList.Count);
+        Assert.AreEqual("Email addresses", ruleList[0].Description);
+        Assert.AreEqual("Social Security Numbers", ruleList[1].Description);
+        Assert.AreEqual("Credit card numbers", ruleList[2].Description);
+        Assert.AreEqual("Phone numbers", ruleList[3].Description);
+    }
+
+    [DataTestMethod]
+    [DataRow("Contact me at john.doe@contoso.com", "Contact me at [EMAIL_REDACTED]")]
+    [DataRow("Contact me at a_b-c%2@foo-bar.example.co.uk", "Contact me at [EMAIL_REDACTED]")]
+    [DataRow("My email is john@sub-domain.contoso.com.", "My email is [EMAIL_REDACTED].")]
+    [DataRow("Two: a@b.com and c@d.org", "Two: [EMAIL_REDACTED] and [EMAIL_REDACTED]")]
+    [DataRow("No email here", "No email here")]
+    public void EmailRules_ShouldMaskEmailAddresses(string input, string expected)
+    {
+        // Arrange
+        var provider = new PiiRuleProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("Call me at 123-456-7890", "Call me at [PHONE_REDACTED]")]
+    [DataRow("My number is (123) 456-7890.", "My number is [PHONE_REDACTED].")]
+    [DataRow("Office: +1 123 456 7890", "Office: [PHONE_REDACTED]")]
+    [DataRow("Two numbers: 123-456-7890 and +420 777123456", "Two numbers: [PHONE_REDACTED] and [PHONE_REDACTED]")]
+    [DataRow("Czech phone +420 777 123 456", "Czech phone [PHONE_REDACTED]")]
+    [DataRow("Slovak phone +421 777 12 34 56", "Slovak phone [PHONE_REDACTED]")]
+    [DataRow("No phone number here", "No phone number here")]
+    public void PhoneRules_ShouldMaskPhoneNumbers(string input, string expected)
+    {
+        // Arrange
+        var provider = new PiiRuleProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("My SSN is 123-45-6789", "My SSN is [SSN_REDACTED]")]
+    [DataRow("No SSN here", "No SSN here")]
+    public void SsnRules_ShouldMaskSsn(string input, string expected)
+    {
+        // Arrange
+        var provider = new PiiRuleProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("My credit card number is 1234-5678-9012-3456", "My credit card number is [CARD_REDACTED]")]
+    [DataRow("My credit card number is 1234567890123456", "My credit card number is [CARD_REDACTED]")]
+    [DataRow("No credit card here", "No credit card here")]
+    public void CreditCardRules_ShouldMaskCreditCardNumbers(string input, string expected)
+    {
+        // Arrange
+        var provider = new PiiRuleProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("Error code: 0x80070005", "Error code: 0x80070005")]
+    [DataRow("Error code: -2147467262", "Error code: -2147467262")]
+    [DataRow("GUID: 123e4567-e89b-12d3-a456-426614174000", "GUID: 123e4567-e89b-12d3-a456-426614174000")]
+    [DataRow("Timestamp: 2023-10-05T14:32:10Z", "Timestamp: 2023-10-05T14:32:10Z")]
+    [DataRow("Version: 1.2.3", "Version: 1.2.3")]
+    [DataRow("Version: 10.0.22631.3448", "Version: 10.0.22631.3448")]
+    [DataRow("MAC: 00:1A:2B:3C:4D:5E", "MAC: 00:1A:2B:3C:4D:5E")]
+    [DataRow("Date: 2023-10-05", "Date: 2023-10-05")]
+    [DataRow("Date: 05/10/2023", "Date: 05/10/2023")]
+    public void PiiRuleProvider_ShouldNotOverRedact(string input, string expected)
+    {
+        // Arrange
+        var provider = new PiiRuleProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+}

src/modules/cmdpal/Tests/Microsoft.CmdPal.Core.Common.UnitTests/Services/Sanitizer/SecretKeyValueRulesProviderTests.cs

@@ -0,0 +1,266 @@
+// 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.UnitTests.TestUtils;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Common.UnitTests.Services.Sanitizer;
+
+[TestClass]
+public class SecretKeyValueRulesProviderTests
+{
+    [TestMethod]
+    public void GetRules_ShouldReturnExpectedRules()
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var rules = provider.GetRules();
+
+        // Assert
+        var ruleList = new List<SanitizationRule>(rules);
+        Assert.AreEqual(1, ruleList.Count);
+        Assert.AreEqual("Sensitive key/value pairs", ruleList[0].Description);
+    }
+
+    [DataTestMethod]
+    [DataRow("password=secret123", "password= [REDACTED]")]
+    [DataRow("passphrase=myPassphrase", "passphrase= [REDACTED]")]
+    [DataRow("pwd=test", "pwd= [REDACTED]")]
+    [DataRow("passwd=pass1234", "passwd= [REDACTED]")]
+    public void SecretKeyValueRules_ShouldMaskPasswordSecrets(string input, string expected)
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("token=abc123def456", "token= [REDACTED]")]
+    [DataRow("access_token=token_value", "access_token= [REDACTED]")]
+    [DataRow("refresh-token=refresh_value", "refresh-token= [REDACTED]")]
+    [DataRow("id token=id_token_value", "id token= [REDACTED]")]
+    [DataRow("bearer token=bearer_value", "bearer token= [REDACTED]")]
+    [DataRow("session token=session_value", "session token= [REDACTED]")]
+    public void SecretKeyValueRules_ShouldMaskTokens(string input, string expected)
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("api key=my_api_key", "api key= [REDACTED]")]
+    [DataRow("api-key=key123", "api-key= [REDACTED]")]
+    [DataRow("api_key=secret_key", "api_key= [REDACTED]")]
+    [DataRow("x-api-key=api123", "x-api-key= [REDACTED]")]
+    [DataRow("x api key=key456", "x api key= [REDACTED]")]
+    [DataRow("client id=client123", "client id= [REDACTED]")]
+    [DataRow("client-secret=secret123", "client-secret= [REDACTED]")]
+    [DataRow("consumer secret=secret456", "consumer secret= [REDACTED]")]
+    public void SecretKeyValueRules_ShouldMaskApiCredentials(string input, string expected)
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("subscription key=sub_key_123", "subscription key= [REDACTED]")]
+    [DataRow("instrumentation key=instr_key", "instrumentation key= [REDACTED]")]
+    [DataRow("account key=account123", "account key= [REDACTED]")]
+    [DataRow("storage account key=storage_key", "storage account key= [REDACTED]")]
+    [DataRow("shared access key=sak123", "shared access key= [REDACTED]")]
+    [DataRow("SAS token=sas123", "SAS token= [REDACTED]")]
+    public void SecretKeyValueRules_ShouldMaskCloudPlatformKeys(string input, string expected)
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("connection string=Server=localhost;Pwd=pass", "connection string= [REDACTED]")]
+    [DataRow("conn string=conn_value", "conn string= [REDACTED]")]
+    [DataRow("storage connection string=connection_value", "storage connection string= [REDACTED]")]
+    public void SecretKeyValueRules_ShouldMaskConnectionStrings(string input, string expected)
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("private key=pk123", "private key= [REDACTED]")]
+    [DataRow("certificate password=cert_pass", "certificate password= [REDACTED]")]
+    [DataRow("client certificate password=cert123", "client certificate password= [REDACTED]")]
+    [DataRow("pfx password=pfx_pass", "pfx password= [REDACTED]")]
+    public void SecretKeyValueRules_ShouldMaskCertificateSecrets(string input, string expected)
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("aws access key id=AKIAIOSFODNN7EXAMPLE", "aws access key id= [REDACTED]")]
+    [DataRow("aws secret access key=wJalrXUtnFEMI/K7MDENG/bPxRfiCYEXAMPLEKEY", "aws secret access key= [REDACTED]")]
+    [DataRow("aws session token=session_token_value", "aws session token= [REDACTED]")]
+    public void SecretKeyValueRules_ShouldMaskAwsKeys(string input, string expected)
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("password=\"complexPassword123!\"", "password= \"[REDACTED]\"")]
+    [DataRow("api-key='secret-key'", "api-key= '[REDACTED]'")]
+    [DataRow("token=\"bearer_token_value\"", "token= \"[REDACTED]\"")]
+    public void SecretKeyValueRules_ShouldPreserveQuotesAroundRedactedValue(string input, string expected)
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("PASSWORD=secret", "PASSWORD= [REDACTED]")]
+    [DataRow("Api-Key=key123", "Api-Key= [REDACTED]")]
+    [DataRow("CLIENT_ID=client123", "CLIENT_ID= [REDACTED]")]
+    [DataRow("Pwd=pass123", "Pwd= [REDACTED]")]
+    public void SecretKeyValueRules_ShouldBeCaseInsensitive(string input, string expected)
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("regularKey=regularValue", "regularKey=regularValue")]
+    [DataRow("config=myConfig", "config=myConfig")]
+    [DataRow("hostname=server.example.com", "hostname=server.example.com")]
+    [DataRow("port=8080", "port=8080")]
+    public void SecretKeyValueRules_ShouldNotRedactNonSecretKeyValuePairs(string input, string expected)
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("password:secret123", "password: [REDACTED]")]
+    [DataRow("api key:api_key_value", "api key: [REDACTED]")]
+    [DataRow("client_secret:secret_value", "client_secret: [REDACTED]")]
+    public void SecretKeyValueRules_ShouldSupportColonSeparator(string input, string expected)
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("password = secret123", "password= [REDACTED]")]
+    [DataRow("api key  =  api_key_value", "api key= [REDACTED]")]
+    [DataRow("token : token_value", "token: [REDACTED]")]
+    public void SecretKeyValueRules_ShouldHandleWhitespace(string input, string expected)
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("password=secret API_KEY=key config=myConfig", "password= [REDACTED] API_KEY= [REDACTED] config=myConfig")]
+    [DataRow("client_id=id123 name=admin pwd=pass123", "client_id= [REDACTED] name=admin pwd= [REDACTED]")]
+    public void SecretKeyValueRules_ShouldHandleMultipleKeyValuePairsInSingleString(string input, string expected)
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+
+    [DataTestMethod]
+    [DataRow("cosmos db key=cosmos_key", "cosmos db key= [REDACTED]")]
+    [DataRow("service principal secret=sp_secret", "service principal secret= [REDACTED]")]
+    [DataRow("shared access signature=sas_signature", "shared access signature= [REDACTED]")]
+    public void SecretKeyValueRules_ShouldMaskServiceSpecificSecrets(string input, string expected)
+    {
+        // Arrange
+        var provider = new SecretKeyValueRulesProvider();
+
+        // Act
+        var result = SanitizerTestHelper.ApplyRules(input, provider.GetRules());
+
+        // Assert
+        Assert.AreEqual(expected, result);
+    }
+}

src/modules/cmdpal/Tests/Microsoft.CmdPal.Core.Common.UnitTests/TestUtils/SanitizerTestHelper.cs

@@ -0,0 +1,110 @@
+// 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.Text.RegularExpressions;
+using Microsoft.CmdPal.Core.Common.Services.Sanitizer.Abstraction;
+
+namespace Microsoft.CmdPal.Common.UnitTests.TestUtils;
+
+/// <summary>
+/// Test-only helpers for applying SanitizationRule sets without relying on production ITextSanitizer implementation.
+/// </summary>
+public static class SanitizerTestHelper
+{
+    /// <summary>
+    /// Applies the provided rules to the input, in order, mimicking the production sanitizer behavior closely
+    /// but without any external dependencies.
+    /// </summary>
+    public static string ApplyRules(string? input, IEnumerable<SanitizationRule> rules)
+    {
+        if (string.IsNullOrEmpty(input))
+        {
+            return input ?? string.Empty;
+        }
+
+        var result = input;
+        foreach (var rule in rules ?? [])
+        {
+            try
+            {
+                var previous = result;
+                result = rule.Evaluator is null
+                    ? rule.Regex.Replace(previous, rule.Replacement ?? string.Empty)
+                    : rule.Regex.Replace(previous, rule.Evaluator);
+
+                // Guardrail to avoid accidental mass-redaction from a faulty rule
+                if (result.Length < previous.Length * 0.3)
+                {
+                    result = previous;
+                }
+            }
+            catch (RegexMatchTimeoutException)
+            {
+                // Ignore timeouts in tests
+            }
+        }
+
+        return result;
+    }
+
+    /// <summary>
+    /// Creates a lightweight sanitizer instance backed by the given rules.
+    /// Useful when a component expects an ITextSanitizer, but you want deterministic behavior in tests.
+    /// </summary>
+    public static ITextSanitizer CreateSanitizer(IEnumerable<SanitizationRule> rules)
+        => new InlineSanitizer(rules);
+
+    private sealed class InlineSanitizer : ITextSanitizer
+    {
+        private readonly List<SanitizationRule> _rules;
+
+        public InlineSanitizer(IEnumerable<SanitizationRule> rules)
+        {
+            _rules = rules?.ToList() ?? [];
+        }
+
+        public string Sanitize(string? input) => ApplyRules(input, _rules);
+
+        public void AddRule(string pattern, string replacement, string description = "")
+        {
+            var rx = new Regex(pattern, RegexOptions.Compiled | RegexOptions.CultureInvariant);
+            _rules.Add(new SanitizationRule(rx, replacement, description));
+        }
+
+        public void RemoveRule(string description)
+        {
+            _rules.RemoveAll(r => r.Description.Equals(description, StringComparison.OrdinalIgnoreCase));
+        }
+
+        public IReadOnlyList<SanitizationRule> GetRules() => _rules.AsReadOnly();
+
+        public string TestRule(string input, string ruleDescription)
+        {
+            var rule = _rules.FirstOrDefault(r => r.Description.Contains(ruleDescription, StringComparison.OrdinalIgnoreCase));
+            if (rule.Regex is null)
+            {
+                return input;
+            }
+
+            try
+            {
+                if (rule.Evaluator is not null)
+                {
+                    return rule.Regex.Replace(input, rule.Evaluator);
+                }
+
+                if (rule.Replacement is not null)
+                {
+                    return rule.Regex.Replace(input, rule.Replacement);
+                }
+            }
+            catch
+            {
+                // Ignore exceptions for test determinism
+            }
+
+            return input;
+        }
+    }
+}

src/modules/cmdpal/Tests/Microsoft.CmdPal.Ext.Calc.UnitTests/CloseOnEnterTests.cs

@@ -19,6 +19,7 @@ public class CloseOnEnterTests
     {
         var settings = new Settings(closeOnEnter: true);
         TypedEventHandler<object, object> handleSave = (s, e) => { };
+        TypedEventHandler<object, object> handleReplace = (s, e) => { };
 
         var item = ResultHelper.CreateResult(
             4m,
@@ -26,7 +27,8 @@ public class CloseOnEnterTests
             CultureInfo.CurrentCulture,
             "2+2",
             settings,
-            handleSave);
+            handleSave,
+            handleReplace);
 
         Assert.IsNotNull(item);
         Assert.IsInstanceOfType(item.Command, typeof(CopyTextCommand));
@@ -41,6 +43,7 @@ public class CloseOnEnterTests
     {
         var settings = new Settings(closeOnEnter: false);
         TypedEventHandler<object, object> handleSave = (s, e) => { };
+        TypedEventHandler<object, object> handleReplace = (s, e) => { };
 
         var item = ResultHelper.CreateResult(
             4m,
@@ -48,7 +51,8 @@ public class CloseOnEnterTests
             CultureInfo.CurrentCulture,
             "2+2",
             settings,
-            handleSave);
+            handleSave,
+            handleReplace);
 
         Assert.IsNotNull(item);
         Assert.IsInstanceOfType(item.Command, typeof(SaveCommand));

src/modules/cmdpal/Tests/Microsoft.CmdPal.Ext.Calc.UnitTests/ExtendedCalculatorParserTests.cs

@@ -65,6 +65,9 @@ public class ExtendedCalculatorParserTests : CommandPaletteUnitTestBase
             ["log10(3)", 0.47712125471966M],
             ["ln(e)", 1M],
             ["cosh(0)", 1M],
+            ["1*10^(-5)", 0.00001M],
+            ["1*10^(-15)", 0.0000000000000001M],
+            ["1*10^(-16)", 0M],
         ];
 
     [DataTestMethod]
@@ -192,9 +195,11 @@ public class ExtendedCalculatorParserTests : CommandPaletteUnitTestBase
     private static IEnumerable<object[]> Interpret_MustReturnExpectedResult_WhenCalled_Data =>
         [
 
-            // ["factorial(5)", 120M], ToDo: this don't support now
-            // ["sign(-2)", -1M],
-            // ["sign(2)", +1M],
+            ["factorial(5)", 120M],
+            ["5!", 120M],
+            ["(2+3)!", 120M],
+            ["sign(-2)", -1M],
+            ["sign(2)", +1M],
             ["abs(-2)", 2M],
             ["abs(2)", 2M],
             ["0+(1*2)/(0+1)", 2M], // Validate that division by "(0+1)" is not interpret as division by zero.
@@ -221,6 +226,9 @@ public class ExtendedCalculatorParserTests : CommandPaletteUnitTestBase
         [
             ["0.2E1", "en-US", 2M],
             ["0,2E1", "pt-PT", 2M],
+            ["3.5e3 + 2.5E2", "en-US", 3750M],
+            ["3,5e3 + 2,5E2", "fr-FR", 3750M],
+            ["1E3-1E3/1.5", "en-US", 333.333333333333371M],
         ];
 
     [DataTestMethod]
@@ -389,4 +397,17 @@ public class ExtendedCalculatorParserTests : CommandPaletteUnitTestBase
         Assert.IsNotNull(result);
         Assert.AreEqual(expectedResult, result);
     }
+
+    [DataTestMethod]
+    [DataRow("171!")]
+    [DataRow("1000!")]
+    public void Interpret_ReturnsError_WhenValueOverflowsDecimal(string input)
+    {
+        var settings = new Settings();
+
+        CalculateEngine.Interpret(settings, input, CultureInfo.InvariantCulture, out var error);
+
+        Assert.IsFalse(string.IsNullOrEmpty(error));
+        Assert.AreNotEqual(null, error);
+    }
 }

src/modules/cmdpal/Tests/Microsoft.CmdPal.Ext.Calc.UnitTests/IncompleteQueryTests.cs

@@ -0,0 +1,38 @@
+// 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.Calc.Helper;
+using Microsoft.VisualStudio.TestTools.UnitTesting;
+
+namespace Microsoft.CmdPal.Ext.Calc.UnitTests;
+
+[TestClass]
+public class IncompleteQueryTests
+{
+    [DataTestMethod]
+    [DataRow("2+2+", "2+2")]
+    [DataRow("2+2*", "2+2")]
+    [DataRow("sin(30", "sin(30)")]
+    [DataRow("((1+2)", "((1+2))")]
+    [DataRow("2*(3+4", "2*(3+4)")]
+    [DataRow("(1+2", "(1+2)")]
+    [DataRow("2*(", "2")]
+    [DataRow("2*(((", "2")]
+    public void TestTryGetIncompleteQuerySuccess(string input, string expected)
+    {
+        var result = QueryHelper.TryGetIncompleteQuery(input, out var newQuery);
+        Assert.IsTrue(result);
+        Assert.AreEqual(expected, newQuery);
+    }
+
+    [DataTestMethod]
+    [DataRow("")]
+    [DataRow("   ")]
+    public void TestTryGetIncompleteQueryFail(string input)
+    {
+        var result = QueryHelper.TryGetIncompleteQuery(input, out var newQuery);
+        Assert.IsFalse(result);
+        Assert.AreEqual(input, newQuery);
+    }
+}