Running WinNT Apps on MacOS

There are multiple ways a Microsoft WinNT applications can be executed on MacOS. Some of tested methods are outlined below.

Running WinNT apps via Wineskin Winery

Wineskin Winery is a user-friendly tool used to make Wine-wrapped ports of Windows apps/software for latest Apple macOS systems. The official GitHub repository is located at Gcenx/WineskinServer.

• Install Wineskin Winery using Homebrew

brew install --cask --no-quarantine gcenx/wine/wineskin

• Open Wineskin Winery app. on your MacOS using Spotlight
• Once Wineskin Winery is opened, you should see a list of Installed Engines
• Click on the + New Engine(s) available! plus icon and download the latest engine version
  • Ie. engine file WS12WineCX64Bit23.7.1 to select CX = CrossOver version
• Select one of the installed and available engines in Wineskin Winery

Wineskin Winery - Selecting the Engines

• Click on the Create New Blank Wrapper button to create a new wrapper
  • Name the wrapper to whatever name you want, ie. Example_MyAppWrapper * (.app)
• Click on the “OK” button and wait until the newly wrapper is created. Note It may take some long time!

Wineskin Winery - Creating the Wrapper

All new created wrappers are located in the following directory:

$ ls -la $HOME/Applications/Wineskin/
# ...
drwxrwxrwx  3 hxxxx  wheel    96 Apr 26 00:20 Example_MyAppWrapper.app
drwxrwxrwx  3 hxxxx  wheel    96 Apr 26 00:20 MyCoolWrapper.app

Wineskin Winery - Wrapper Created

• Open the newly created wrapper app. using Finder or Spotlight
• You should be presented with Wineskin Popup, that allows you to install WinNT apps or configure Wine

Wineskin Winery - Wrapper Popup

• If using Wineskin Winery for WindowsNT Games, click on Winetricks in the popup and search for:
  • d3dcompiler_47, dxvk (DirectX) DLLs or any version above
• If using Wineskin Winery for WindowsNT Apps, click on Winetricks in the popup and search for:
  • vcrun2022 or other required DLL for Visual C++ libraries
  • dotnet48 or other required DLL for MS .NET libraries
• Otherwise, use FanderWasTaken/wine-dependency-hell-solver to solve required complex dependencies
• Click on Run to install selected Winetricks/DLLs and wait for process to finish
• You can also use Winetricks to download common WinNT apps such is 7Zip et al.

Wineskin Winery - Using Winetricks to install requirements

Wineskin Winery - Using Winetricks (Installation)

• Back in the Wrapper Popup window, click on the “Install Software” button
• Select either of the options in the “Wineskin Installer” window
  • Choose Setup Executable: to install WinNT apps/games via setup.exe or other installer
  • Copy a Folder Inside: to install portable programs by copying a folder inside the wrapper
  • Move a Folder Inside: same as copy, except it moves the folder instead of copying it

Wineskin Winery - Installer

• Most likely, you will use the first option (Choose Setup Executable)
• Click the Choose Setup Executable button in Installer to select setup.exe file or equivalent
• Complete the installation using the shown windows/popups

Wineskin Winery - Selecting Telegram Desktop Setup

Wineskin Winery - Installing Telegram Desktop

• Once the Game/App is installed in Wineskin Winery, click on the “Advanced” button in “Wineskin Popup”
• In Wineskin Advanced window, configure:
  • Windows app: to path location of the App executable inside the Windows (use Browse button)
  • In Tools tab, you may:
    • Use Config Utility via winecfg
    • Use Registry Editor via regedit
    • Use Task Manager or Command Line via taskmgr/cli
    • Open Control Panel via control and much more

Wineskin Winery - Wineskin Advanced - Configuration

Wineskin Winery - Wineskin Advanced - Tools

If the Wineskin Wrapper is crashing, ie. app can’t be opened, you may reconfigure the Wrapper by going to:

• Wineskin Wrapper dir: /Users/$USER/Applications/Wineskin/
• Right-click on crashing wrapper, and click Show Package Contents
• Double-click on the Wineskin.app file inside the enclosed wrapper package folder
• Re-configure Wineskin and fix crashing via Reinstall/Advanced/DLLs/etc.

References

• Wineskin as Crossover alternative on M1
• Play DOOM 3 natively on Apple M1
• Play SIMS on Mac
• Debugging game on MacOS via wine
• /r/FitGirlRepack, /r/PiratedGames

Running WinNT apps via Whisky

Whisky is a modern Wine wrapper for macOS built with SwiftUI. The official GitHub repository is located at Whisky-App/Whisky.

• Install Whisky using Homebrew

brew install --cask whisky

• Whisky Official Documentation
• Whisky Game Support