Run your favorite Windows operating system programs direct on any computer, including Mac and Linux systems. When using any operating system, you often encounter a program you like that isn't available for your system. That's where virtual systems are your best friend. Wine is a translator for Windows API, turning it into POSIX in real-time.

Wine is a fantastic tool for Mac users and there is a number of ways to get it working but possibly the best way is also the most complex. That being said once it’s setup you can use a big number of Windows applications on your Mac.

The easiest way to get Wine on your Mac is also the most expensive and least control of all. Crossover Mac (http://www.codeweavers.com) is a commercial variant of Wine that installs a really nice bottle creator (a bottle is a self contained VM). There is also WinOnX which has a Cocoa interface for Wine and is available on the Mac App Store but has a couple of issues with some applications. I suspect these are a result of them not using the latest versions of Wine which is the biggest problem with something like this as third parties need to do a lot of testing and by then the main software (Wine in this case) has been updated a number of times.

So the best option is to install Wine yourself but this does require a lot of getting your hands dirty and will require some tools for you to download. The first is Xcode which is available as a free download on the Mac App Store. It’s a big download though so here’s hoping your internet connection is good.

• Wine (originally an acronym for 'Wine Is Not an Emulator') is a compatibility layer capable of running Windows applications on several POSIX. Published on Jun 24, 2018 To run.exe files on Mac you need to use Wine or Winebottler. Wine will let you run the exe directly, whereas Wine bottler will package the.exe into a macOS app that you.
• Wine allows OS X users to run Windows applications. Note: this listing is for the official release of Wine, which only provides source code. If you want a version of Wine that is packaged specifically for OS X, then use Winebottler, available here.
• Wine (originally an acronym for 'Wine Is Not an Emulator') is a compatibility layer capable of running Windows applications on several POSIX-compliant operating systems, such as Linux, macOS, & BSD.
• Run your Windows based Programs on your Mac with these vanilla Wine Builds. They are compiled from the sources of winehq.org and they come as a neat.app with my custom starter. For more info on how these Wine.app Builds are generated, have a look at the Tech Specs. If you need something more powerful, try WineBottler.

After this you’ll need to obtain a copy of XQuartz (http://xquartz.macosforge.org/). This is not the Apple version as Apple no longer rolls their own into OS X like they used to. However, this version is officially supported by Apple. Simply download and run the installer.

Once this has been downloaded and installed we’ll use a system called Homebrew. This is a pretty “easy” to use application but it is all command line based so it requires getting things typed just right. This is why I suggest copying and pasting from this page as these links will get you up and running. Open up Terminal (found in Applications / Utilities or if using LaunchPad it’s found in the Other folder). Copy and paste this line into Terminal:

ruby -e “$(curl -fsSL https://raw.github.com/Homebrew/homebrew/go/install)”

This will install Homebrew with the latest version. The prompts are pretty easy to follow so just roll with them. You may need to enter your password so make sure the account you’re using has administrator rights.

It will take a wee while to perform this so don’t worry too much.

Still in Terminal we now can install Wine and its associated WineTricks which installs some packages that helps make Wine work better. Copy and paste this code:

brew install –devel –universal wine winetricks

To highlight what is going on here “brew” is the application you’re running, “install” tells brew to install the following applications. –devel installs the developer version of the following apps. –universal installs the universal version although this isn’t so much of a requirement anymore as most Macs will be running 64 bit apps so you can actually leave this switch out if you want to. “wine” and “winetricks” are the actual applications we are going to get Homebrew to install. Press enter and watch the fun happen. Now you’ll see a number of errors. Don’t worry about these they aren’t anything to be concerned with.

The last bit we need to add to the Terminal is configuring WineTricks. Simply copy and paste this line:

winetricks comctl32 corefonts dotnet40 eufonts gdiplus gdiplus_winxp ie8 msls31 physx pngfilt tahoma vcrun2010 wininet wsh56vb xmllite

This installs a number of various Windows system files and fonts that allows Wine to handle things like games better. Some may already be installed so don’t worry about error messages you’ll receive. Simply just go with the defaults if/when installer windows pop up.

Once this is done we’re going to perform a little trick. In fact I’m going to make it a bit easier for you and will give you a link to a little AppleScript application I created. Simply just download it, unzip it, and copy it to your Applications folder.

What does this do? Simply it is an AppleScript that tells the Terminal to run the Wine Installer application. This is the equivalent to the Add/Remove Programs application in Windows XP. I’m using this from now on simply to make it easier for you because it doesn’t require typing anything in anymore just the locations of the installer files you need.

To install a Windows application simply click on the Install button and find the installer you want to run just like you would on Windows.

Running applications is a little trickier. Once again I recommend using AppleScript here:

Copy and paste this line of text into the editor window:

do shell script “/usr/local/bin/wine

Because running the commands from AppleScript don’t set a default path we need to fully qualify the application path. That’s why the command for Wine is /usr/local/bin/wine. In Terminal we simply just type “wine …” where “…” is the path of the Windows application we want to run.

Say I want to run the Watchtower Library that I have installed so that I can do some personal Bible study. If I enter this line into AppleScript editor and ran it it would run WTLibrary for me:

do shell script “/usr/local/bin/wine ‘/Users/darrynlowe/.wine/drive_c/Program Files/Watchtower/Watchtower Library 2013/E/wtlibrary.exe'”

Notice the ‘’ around ‘/Users/darrynlowe/.wine/drive_c/Program Files/Watchtower/Watchtower Library 2013/E/wtlibrary.exe’. This is incredibly important because if you don’t put it in all the spaces in the path will cause everything to stop. UNIX doesn’t like spaces in path names.

Save this AppleScript to your Applications folder but make sure you save it as an application:

This way it won’t open any windows other than what it needs to.

Now you’ll notice something here as you would have with the Wine Installer screenshot:

The windows look like Windows applications but they don’t look quite like the Windows applications and they don’t look like Mac windows either. This is because the windowing system being used is X11 (XQuartz). X11 is a UNIX windowing system and will be used because Wine itself is a UNIX application not a Mac one. This raises one issue for Mac users. Because it’s UNIX based and because the original app is a Windows one key mappings are incorrect. For example if you are wanting to copy and paste between Mac and apps in Wine you’d have to use CTRL instead of Command so Copy would be CTRL + C instead of the Mac Command + C however when you go to paste into a Mac app you’d have to use Command + V were as in the app running in Wine you’d have to use CTRL + V. It will get confusing incredibly quickly. This is where CrossOver has the advantage because it maps everything to Mac keys so you don’t have to think in two different environments.

The big question is though is Wine better than a VM like Parallels or VMWare? Short answer is no as these run actual versions of Windows and are thus more capable than Wine. However, these have big performance hits and can slow down your machines to ludicrously slow speeds whereas Wine doesn’t seem to have the same performance issues. However Wine won’t run all applications and thus isn’t as brilliant as Parallels say. Ultimately this method is somewhat convoluted but the advantage over Parallels or VMWare is that it doesn’t require a Windows license to run Windows apps.

Head over to http://appdb.winehq.org to see if the app you want to run will work then have fun if it does.

Note: I know this is an old thread, and am just posting to help anyone else who stumbles upon this thread.

First of all: Wine (just plain wine) is NOT available for Mac, so that leave you with Wineskin, WineBottler, PlayOnMac, or CrossOver.

Wineskin and WineBottler are intended for creating wrappers, which is basically converting it to a Mac application.

Wineskin gives you more customization over your wrapper.

WineBottler also comes with a system that lets you just run any exe on mac just like that.

What Is Wine For Mac

PlayOnMac lets you download and run supported apps easily, but isn't good for just any exe.

Wine Mac App

CrossOver is paid software.

Xquartz For Mac

Wine Mac Catalina

If all you want to do is run exes with right-click>Open With, than install WineBottler.