The above is the Winehq way to install wine on mac but that makes it cumbersome to use considering you must launch the Wine Stable, Wine Devel or Wine Staging app each time to get access to wine within Terminal Wine basics If your intention is to have a more stable environment use wine-stable Grab a wine package usually using the latest wine-devel is recommended, but most agree it's best to use the latest wine-staging due to additional patches. How to manually install wine on mac using Winehq releases This command will add my brew tap and the second command will install my custom cask of Wine Staging The tap contains the following Brew install -cask -no-quarantine gcenx-wine-staging