Run Windows executables on Mac using Wine

May 21, 2011 by

No, not the wine that you drink, the kind that lets Windows applications run on UNIX OSes.  Today, Windows and Mac play nice together; you can dual-boot Windows on your Mac or run it within a virtual machine. A virtual machine allows a guest OS to be installed to a virtual hard disk on your computer. This can be great and you’ll get full access to what Windows has to offer, but when you already have a Mac, the only thing you would need is to run an EXE or an MSI file.

Unfortunately,  a new version of Windows will set you back about $200 dollars ($160 more than Snow Leopard), and you probably don’t like Windows enough to spend that much on an insecure, non-UNIX operating system. Wine makes it easy to run almost any Windows executable file on your Mac.



Before you begin, you will need a few things.

  • An Intel Mac
  • An admin account (most likely set up during initial configuration)
  • An Apple developer account
  • Xcode (You can install Xcode from your Mac OS X installation DVD, or you can download it from the App Store or from the Apple Dev Center
  • X11 (Comes on Snow Leopard by default. On Leopard, it must be installed from the Mac OS X Installation DVD)
  • Java Development package (Also comes by default. If you need an update or a fresh install, download for 10.6 or 10.5)
  • An internet connection, preferably ethernet (If you’re reading this, you are all set)
  • About an hour

Install MacPorts

  1. Download the MacPorts DMG file
  2. Follow the instructions on the installer

Configure MacPorts

1. Open up terminal and copy and paste the following command:

echo export PATH=/opt/local/bin:/opt/local/sbin:\$PATH$'\n'export MANPATH=/opt/local/man:\$MANPATH | sudo tee -a /etc/profile

The Terminal will ask for your password: this is the password to the Admin account on your computer. As a security measure, the Terminal does not display anything as you type, not even asterisks. Type your password anyway, and press enter. If you ran the command correctly, the Terminal should respond with:

export PATH=/opt/local/bin:/opt/local/sbin:$PATH
export MANPATH=/opt/local/man:$MANPATH

2. Next, run this command:

if [ `sysctl -n hw.cpu64bit_capable` -eq 1 ] ; then echo "+universal" | sudo tee -a /opt/local/etc/macports/variants.conf; else echo "not 64bit capable"; fi

This just gives MacPorts some compatibility information.

3.Close the current Terminal window and open a new one

Install Wine and its dependencies

To install Wine using MacPorts, use this command:

sudo port install wine

You may be asked to enter your password again. When the install begins, you will see a long list of dependencies. The dependencies and eventually, Wine, will install. If it seems to hang at times, just be very patient. Go have a snack, take a shower, start a business, take over the world or anything else you do in your spare time. When you see something like:

Will-Coughlins-MacBook-Pro:~ willcoughlin$

and you are able to enter commands, then it is done and you may begin using Wine.

Using Wine to open programs

To open an executable file, simply use Terminal to navigate to the containing directory and run the following command:

wine $PROGRAM.exe

where $PROGRAM equals the name of your program. If you had a program called Notepad.exe, then the command would be:

wine Notepad.exe

If installed correctly, X11 will open (if it isn’t already), and the program will pop up, ready to use!

Author’s notes

  • For extended support, install Mono to support the .NET framework

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