Executable files, more commonly known as EXE files, are mainly for Windows PCs. They tell the computer to run something. However, you can use them on a Mac; many macOS users have run EXE files in the past. We’ll show you how to open executables on any Mac with a Wine frontend, which most people would recommend.
RAPID RESPONSE
To open executable files on macOS, the easiest method is to install CrossOver. Once installed, click with two fingers on your EXE, select open with, and select CrossOver† Use CrossOver to install or run an executable.
SKIP TO IMPORTANT SECTIONS
Why is it so hard to install or launch executable files on Mac?
Joe Hindy / Android Authority
Executable files are not complicated pieces of software. They simply tell your computer to run a specific set of commands, open specific files, or do specific things. But macOS can’t read what EXE files are trying to say. It’s a bit like reading a foreign language. You know how to read English, but you may not know how to read Arabic. Running EXE files on macOS is like an English reader trying to read Arabic.
Running EXE files on a Mac is like asking someone to read a foreign language they don’t know.
Since macOS itself cannot read EXE files, it needs a little help. The most popular and effective help you can find is Wine. Simply put, Wine helps macOS computers impersonate Windows computers so they can run EXE files. It’s a bit of an oversimplification, but that’s the general idea.
It really isn’t more complicated than that. Apple could theoretically add support for EXE files, but that would require them to use code commonly found in Windows. That would probably
How to open executable files with PlayOnMac
PlayOnMac is a Wine frontend with a fairly user-friendly GUI. You can run executable files, install apps and do other things with it. We don’t think it’s as clean or easy to use as CrossOver, but it’s free, so it’s the one we’ll recommend first.
The installation process is involved, so read the instructions carefully, go step by step and try not to rush through it.
Requirements
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You need to install a few things before you can use PlayOnMac. Open the Terminal and type the following commands. Of course, hit enter after typing each command.
- sudo spctl –master-disable
- Enter your password and press enter again. This disables software gatekeeping and prevents problems from occurring later.
- bin/bash -c “$curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)”
- Enter your password and press enter when prompted. This command installs Homebrew, a necessary step for PlayOnMac. The installation only takes a few minutes.
- Pro tip — If the Homebrew commands below do not work due to a “command not found” problem, type export PATH=/opt/homebrew/bin:$PATH and press enter. After that, the commands should work.
- brew tap homebrew/cask versions
- brew install -barrel -wine-stable without quarantine
- The two commands above will install the latest version of Wine on your Mac.
- brewing installation -cask xquartz
- The last command will install XQuartz on your system. Newer versions of PlayOnMac shouldn’t require XQuartz, but it doesn’t hurt to install it. Make sure you have completed all of the above commands before continuing.
How to install executable files with PlayOnMac
Joe Hindy / Android Authority
- You have to do four things before you can continue.
- Download the latest PlayOnMac version from the official website.
- Open the DMG file and click and drag the PlayOnMac log into the Applications folder to properly install the DMG.
- Once you are done, go to your download folder and click with two fingers on the EXE you want to install, select Open withand select PlayOnMac† If there is a prompt, just press Open continue.
- PlayOnMac will analyze your EXE file and give you the option to install it on your computer. Just follow the directions. All you have to do is type the name of the application you are installing during the process.
- Once PlayOnMac has everything under control, proceed with the installation of the app itself. Each app’s installer is different, so just follow the instructions and make sure you read everything.
- Once installed, PlayOnMac gives you the option to create a desktop shortcut. We don’t think it’s necessary, but you can if you want.
- To launch the app, open PlayOnMac and your installed apps should appear on the main page. Tap the app and click Run in the left margin to open it.
Pro tip — The above process works for executables that install full applications or just run the app without installing anything.
PlayOnMac is the best free option available, but it also has a pretty frustrating and complicated installation process. The good news is that when you’re done, you’ll have Wine and Homebrew on your machine, which is handy for other things.
How to open executable files with CrossOver
The easiest method to run EXE files is with CrossOver. CrossOver is an app from CodeWeavers, Wine’s official corporate sponsor. It hosts the website and employs many Wine developers. So CrossOver is as close to an official Wine app as you can find.
How to install executable files with CrossOver
- go to CrossOver and download the free trial of the application. It should work on all modern Macs.
- Open the downloaded file and install CrossOver. It’s a linear process, so keep going until it’s installed and opened.
- Once the installation is complete, locate your EXE file and click on it with two fingers.
- Select Open with and then CrossOver†
- CrossOver opens and offers to install the file.
- If the previous step doesn’t happen, you can open CrossOver and search for the app you want to install. The app seems to recognize when you have the EXE file in your download folder and will offer to install it from there.
- Anyway, press the Get on button once it is ready to use.
- On the next screen, CrossOver will give you some more setup details. Touch to install†
- CrossOver will install the EXE file and you’re good to go.
How to run executables on CrossOver
Joe Hindy / Android Authority
The other thing executables can do is simply run. You’ll find this in very old games, scripts, and other examples. The EXE file does not install anything. It just runs until you leave it. CrossOver can do this too, but it’s a bit tricky.
- Open CrossOver and select Bottle from the menu bar. Touch New bottle†
- below New Bottle Type:select Windows 10 64 bitgive it a name and then press To create†
- Find your new bottle in the left margin and click on it.
- Double click Run command†
- On the next screen, tap the To leaf through button, find your EXE file, select it and tap Open†
- Finally tap Run†
- Your executable should run. To stop, exit the window.
Pro tip — To run a new EXE file, reuse the bottle you created earlier and just run this tutorial again from the Run command step.
Pro tip – During the Run command step, you can choose to hit Save job as a launcher† Doing so will keep it in your bottle for easy recall later. Make sure to only use this option if your EXE file is somewhere safe. Removing the EXE will cause an error, and it won’t open again.
CrossOver is the easiest method we encountered for both actions. The only real downside is that it has a 14 day free trial and after that you have to buy it. There is a $59 per year option or a $499 lifetime purchase option. It’s pricey, but it works pretty well.
Next one: What is Keychain Access on Mac, where to find it and how to reset it?
FAQ
There are dozens of reasons that could be, depending on your system, your configuration and which frontend you are using. We recommend deleting everything and starting from scratch.
We wrote this tutorial using a Macbook running macOS 12.4 Monterey, the most recent macOS at the time of writing. It still works fine, but you should be using a frontend that is still actively being developed, such as PlayOnMac or CrossOver.