Installation Guide

ExtremeGammon on macOS

Running eXtreme Gammon 2 via Wine on macOS

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Background: ExtremeGammon (XG) is a Windows application. On macOS it runs via Wine, a compatibility layer. This guide covers installing Wine and XG together. Wine 11.0 is required — version 11.0_1 is known to cause XG to hang on launch.

Before You Start

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Tested on Apple Silicon only: This guide has been tested on Macs with M1/M2/M3/M4 chips, where Wine runs as an Intel binary under Rosetta 2. It should work on Intel Macs as well — the Rosetta step will simply be skipped.

You will need:

Quick Install

Run this single command in Terminal to install everything — Wine, the Gatekeeper fix, PATH setup, and the XG installer. You'll click through the XG installer GUI to finish.

curl -fsSL https://vlamis.nyc/bg/install-xg.sh | zsh
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You can inspect the script before running it at vlamis.nyc/bg/install-xg.sh. It installs Rosetta 2, Wine 11.0, and XG; adds wine to your PATH; creates an xg shell alias; and installs the app launcher in /Applications. Detects zsh, bash, and fish automatically.

Manual Install

Part 1 — Install Rosetta 2

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Intel Mac users: Skip this step — Rosetta 2 is only needed on Apple Silicon.

Step 1
Install Rosetta 2
softwareupdate --install-rosetta --agree-to-license

If Rosetta is already installed you'll see a message saying so — that's fine, continue.

Part 2 — Install Wine 11.0

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Important: Wine 11.0_1 (the current release) causes XG to hang on launch. You must use Wine 11.0 specifically. Because you're installing it manually rather than through a package manager, it will never auto-upgrade.

Step 2
Download Wine 11.0
curl -L -o ~/Downloads/wine-stable-11.0-osx64.tar.xz \
  https://archive.org/download/wine-stable-11.0-osx64.tar/wine-stable-11.0-osx64.tar.xz
Step 3
Extract Wine to /Applications
tar -xf ~/Downloads/wine-stable-11.0-osx64.tar.xz -C /Applications

This places Wine Stable.app in your Applications folder.

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Gatekeeper: macOS may block Wine Stable.app as an unverified app. If you see a security warning, run this once to clear it: xattr -dr com.apple.quarantine "/Applications/Wine Stable.app"

Step 4
Add Wine to your PATH

So you can run wine from Terminal without typing the full path each time:

zsh (default on modern macOS):

echo 'export PATH="/Applications/Wine Stable.app/Contents/Resources/wine/bin:$PATH"' >> ~/.zshrc
source ~/.zshrc

bash:

echo 'export PATH="/Applications/Wine Stable.app/Contents/Resources/wine/bin:$PATH"' >> ~/.bash_profile
source ~/.bash_profile

fish:

fish_add_path "/Applications/Wine Stable.app/Contents/Resources/wine/bin"
Step 5
Verify Wine is working
wine --version

Should print wine-11.0. If wine is not found, close and reopen Terminal and try again.

Part 3 — Install ExtremeGammon

Step 6
Run the ExtremeGammon installer

First, download xg2install.exe and save it to your Downloads folder. Then run:

wine ~/Downloads/xg2install.exe

The Windows installer UI will appear — proceed through it normally and install to the default location.

Step 7
Launch ExtremeGammon
wine ~/.wine/drive_c/Program\ Files\ \(x86\)/eXtreme\ Gammon\ 2/eXtremeGammon2.exe

XG should launch. See below for how to create a short alias so you don't have to type this each time.

Optional — App Launcher

Instead of using Terminal each time, you can download a pre-built app that launches XG with a double-click from your Dock or Applications folder.

Step 1
Download and install

Download eXtremeGammon.zip, unzip it, and drag eXtremeGammon.app to your Applications folder.

Step 2
Bypass Gatekeeper

Because the app isn't code-signed, macOS will block it on first launch. Right-click the app → Open, then click Open in the dialog that appears. You only need to do this once.

If that doesn't work, go to System Settings → Privacy & Security and click Open Anyway.

Optional — Create a Launch Alias

Add a shortcut to your shell config so you can just type xg to launch:

zsh / bash — add to ~/.zshrc or ~/.bash_profile:

alias xg='echo "Launching eXtreme Gammon — you can close this terminal once XG opens." && nohup wine ~/.wine/drive_c/Program\ Files\ \(x86\)/eXtreme\ Gammon\ 2/eXtremeGammon2.exe > /dev/null 2>&1 &'

Then reload your config (source ~/.zshrc) and you can launch XG by typing xg.

fish:

function xg
    set exe "$HOME/.wine/drive_c/Program Files (x86)/eXtreme Gammon 2/eXtremeGammon2.exe"
    echo "Launching eXtreme Gammon — you can close this terminal once XG opens."
    nohup "/Applications/Wine Stable.app/Contents/Resources/wine/bin/wine" $exe > /dev/null 2>&1 &
end
funcsave xg

Troubleshooting

Problem
No audio in XG

Wine's audio support on macOS requires the GStreamer runtime, installed via Homebrew. If you don't have Homebrew yet:

/bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)"

Follow the prompts. On Apple Silicon, run the two additional commands it shows at the end to add Homebrew to your PATH. Then install GStreamer:

brew install --cask gstreamer-runtime

Then relaunch XG.