How to Open Executable Files on Mac: Virtual Machine, Boot Camp, or Wine

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Open EXE files on Mac in a Windows-like environment or using Wine
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This wikiHow teaches you how to run Windows executable (EXE or .exe) files on a Mac. To do so, you can either install a Wine-based compatibility layer to run EXE files, or install the Windows operating system on your Mac. You can install Windows using a virtual machine, like Parallels (for Macs with Apple silicon processors), or using your Mac's Boot Camp utility (for older Macs with Intel processors).

The Best Options for Running EXE Files on Mac

  • The easiest way to run an EXE file on Mac is to install Windows.
  • If your Mac has an Apple silicon processor, you’ll need to use a virtual machine. For Macs with Intel, use Boot Camp.
  • You can also use Wine (an API compatibility layer) to run Windows software on your Mac.
Method 1
Method 1 of 3:

Parallels (Apple Silicon) and other VMs

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  1. To check, click the
    Mac Apple
    Apple menu button at the top left corner of your screen, then click About This Mac . Look at the line that says Chip . If you see Apple M1 , M2 , or M3 , you’ll need to use Parallels or another virtual machine. These apps work like a virtual Windows desktop on your Mac. If your Mac has an Intel chip, you’ll need to use the Boot Camp method to install Windows instead.
    • Virtual machines like Parallels can run many EXE files, but there may be some they can’t open. VMs use a streamlined version of Windows called Windows on Arm , which is designed for efficiency and can only run a limited number of apps.
    • You can also try the Wine method if you have a newer computer and would rather not use a virtual machine.
  2. Parallels allows you to run a slightly limited version of Windows on your Mac. To install it, go to the Parallels Downloads page and click one of the options ( Buy now or Try free ) to get started.
    • You can also install Parallels from the App Store. [1]
    • While Parallels has a free trial version, you’ll need to pay to use the software for more than 2 weeks.
    • After downloading the software, open the install file and follow the onscreen instructions to install Parallels.
    • If you’re installing the Business Edition of Parallels, you’ll need to set up an account first.
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  3. Once you’ve installed the app, open it. You should now see a Parallels icon in the menu bar at the upper right side of your Mac’s screen.
  4. Select the icon at the top of your screen that looks like a monitor with two parallel vertical lines on its right side. In the dropdown menu, select Control Center .
  5. You’ll see this at the top of the Control Center window.
  6. This option is available in Parallels Desktop 18 and later.
  9. Once the download and installation are complete, you’ll see an Installation Complete screen. Follow the prompts to accept the license agreement terms and finish the process.
  10. By default, you should be able to launch EXE files in Parallels on your Mac simply by double-clicking them. You can also launch Windows in the Parallels Desktop app and open the files from within the app. Open and run the files just like you would on a Windows PC.
  11. 11
    Try VMWare Fusion as a free alternative. Parallels is the only Microsoft-authorized virtual machine that can run Windows on a Mac, which means it may be more secure and reliable than the alternative options on the market. However, if you’re looking for a virtual machine that doesn’t cost a hefty fee, VMWare recently made its Fusion 13 Pro software free for personal use. [2]
    • To get VMWare Fusion Pro, you’ll need to register for an account on the Broadcom Support Portal .
    • Once you’re registered and logged in, head over to this download page . Make sure you select the “for personal use” version of the software.
    • Check out this detailed walkthrough of how to install and run Windows 11 using the VMWare Player.
    • If you go for this option, be aware that it’s a bit more limited than Parallels. VMWare Fusion doesn’t include DirectX 11 support, so it’s not a great option for playing Windows games on your Mac. [3]
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Method 2
Method 2 of 3:

Boot Camp (Intel Processors)

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  1. The Boot Camp utility lets you install Windows on your Mac for free so you can run EXE files. However, you can only install Windows with Boot Camp if your Mac has an Intel processor. For Macs with Apple silicon processors, you’ll need to use the Parallels or Wine method. To find out if your Mac has an Intel processor:
    • Open the
      Mac Apple
      Apple menu and click About This Mac .
    • Look for an item labeled either “Chip” or “Processor.” If you see “Processor” followed by the name of an Intel processor, your Mac will support installing Windows with Boot Camp.
    • Most newer Macs (released in late 2020 or later) have an Apple silicon processor instead.
  2. MacOS' Boot Camp supports Windows 8, 8.1, 10, and 11. [4]
    • You can download an ISO file version of Windows 10 from Microsoft's site here or get a Windows 11 ISO here .
  3. Open your Mac's Utilities folder . You can do this by clicking the magnifying glass icon on the top-right side of your Mac's screen, typing in "Utilities", and then clicking the Utilities folder. [5]
  4. It resembles a grey hard drive. [6]
  5. These steps will entail selecting the Windows installation file, selecting the drive onto which you wish to install Windows , and restarting your Mac.
    • If you're installing Windows from a USB drive , you'll be prompted to insert the drive during this process.
  6. After you finish setting up your Boot Camp settings, you'll be prompted to restart your Mac . When your Mac is done restarting, you should be at the Windows installer screen. [7]
  7. If you're installing Windows from a USB drive, you'll need to select this option to proceed with the installation. [8]
    • If you're installing Windows directly from an ISO file, Boot Camp will partition your drive for you.
  8. This process will vary depending on the version of Windows you're using, but you'll restart your Mac at the end just like you did while setting up the Boot Camp Assistant.
  9. Doing so will load the Startup Manager window. [9]
  10. This window will display all of the different drives from which you can start up your Mac.
  11. Doing so will load your Mac into the Windows operating system.
  12. As long as you're using Windows, EXE files should begin running immediately after double-clicking them.
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Method 3
Method 3 of 3:

Using Wine

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  1. Wine is a compatibility layer that directly translates Windows commands into Mac commands so you can run Windows software without installing a new operating system or using a virtual machine. While you can install Wine directly using Terminal or the free Wine app, it’s a tricky and complicated process getting it to work—especially if you’re running macOS Catalina or later, which requires some additional modifications. Instead, you might want to try one of these third-party apps that are built on Wine but offer a more user-friendly and up-to-date interface:
    • PlayOnMac : This option is free and works with a wide variety of Windows apps.
    • Apple’s Game Porting Toolkit (macOS Sonoma and later) is another option for advanced users. You may be prompted to enroll in the Apple Developer program before you can use it.
    • CrossOver is one of the most popular and user-friendly options, but it’s fairly expensive. However, you can try it free for 14 days before you commit to buying it. As of December 2024, version 24 is compatible with all versions of macOS from Catalina (10.15) to Sequoia (15.0).
  2. Unfortunately, not all EXE files will run even with a compatibility layer installed. Before you attempt to open a file in one of these apps, check the developer’s website to find out if it will work.
    • For instance, you can find a full list of apps compatible with PlayOnMac here .
    • You can search for CrossOver-compatible Windows software using the CrossOver Compatibility database .
  3. The right way to launch an EXE file depends on the software you’re using, but in many cases, you will need to create a “Bottle” or “Skin” to run the Windows file. For example, here’s how you do it in CrossOver: [10]
    • In the CrossOver menu at the top of the screen, select Bottle > New Bottle .
    • Enter a name for the Bottle (typically the name of the app or EXE file you’re trying to open), then click Create .
    • Select your new Bottle from the left sidebar menu, then click Run Command .
    • Click Browse and locate the EXE file on your Mac, then select it and click Open .
    • Click Run to open your file.
    • Click Save Command as a Launcher to make a shortcut icon for the EXE file. That way, you won’t have to go through this process again every time you run the file.
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Community Q&A

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  • Question
    How do I reverse the process so I can run Mac files again?
    Community Answer
    While your computer boots up, hold the option key. Once you see the startup manager, release the option key. Select your original partition and press enter.
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  • Question
    I can't install WineBottler. It said "Image not found. Can't open install application". What can I do?
    Community Answer
    If you are using the newer version of Mac OS X, it's not compatible.
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  • Question
    What do I do if I click open with Wine, check Run Directly In, then click Go, but nothing happens?
    Community Answer
    Use the second method explained in the tutorial. Your executable file (.EXE) most likely doesn't support Wine.
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      References

      1. ↑ https://kb.parallels.com/123801/
      2. ↑ https://blogs.vmware.com/cloud-foundation/2024/05/14/vmware-desktop-hypervisor-pro-apps-now-available-for-personal-use/
      3. ↑ https://youtu.be/za2CyrxKYFs?si=Mjej7-_r8ZhrI7dS&t=23
      4. ↑ https://www.microsoft.com/en-us/software-download/windows10
      5. ↑ https://support.apple.com/en-ph/guide/bootcamp-assistant/bcmp173b3bf2/6.1/mac/13.0
      6. ↑ https://www.softwarehow.com/open-exe-file-mac/
      7. ↑ https://support.apple.com/en-us/102622
      8. ↑ https://support.apple.com/en-ph/guide/bootcamp-assistant/bcmp173b3bf2/6.1/mac/13.0
      9. ↑ https://www.softwarehow.com/open-exe-file-mac/
      1. ↑ https://www.codeweavers.com/support/docs/crossover-mac/

      About This Article

      Article Summary X

      1. Download and install Wine.
      2. Right-click the .EXE.
      3. Click Open With .
      4. Click Wine .
      5. Select Run directly in .
      6. Click Go .

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