This guide explains how to open executable (EXE) files on a Mac. To do this, you can install the free WINE software or set up Windows 8 or 10 using the Boot Camp feature on your Mac.
Steps
Using WINE

Visit the WineBottler website at http://winebottler.kronenberg.org/. WINE is an advanced program, and WineBottler provides a more user-friendly interface for WINE.
- However, some programs are not compatible with WINE. If the EXE file doesn’t run on WINE, you may need to use Boot Camp.

Click on the "WineBottler 1.8-rc4 Development" button. This button is located in the center of the page and has a green arrow icon.
- If you're using an older version of OS X (prior to OS X Capitan), click on WineBottler 1.6.1 Stable.

Click on the Download button when prompted. This action will take you to an advertisement screen.

Click on the SKIP AD button. This option will appear at the top right corner of the screen after 5 seconds.
- Avoid clicking on any other links on this page while waiting for the SKIP AD button to appear.
- If you're using an ad blocker, make sure to disable it on this page first.

Wait for the WineBottler download to complete. If WineBottler doesn’t start downloading automatically after 5 seconds, you can click on the "WineBottlerCombo_1.8-rc4.dmg" link to start the download manually.

Install WineBottler. To do this, double-click the WineBottler installer file, then drag the "Wine" and "WineBottler" icons into the "Applications" folder.

Right-click the EXE file using two fingers. This action will open a menu.

Select Open With from the top section of the dropdown menu.

Click on Wine. You will find this program listed either to the left or right of the choices in the newly displayed window. A warning message will appear.

Make sure the "Run directly in" option is selected. If not, click the circle next to "Run directly in [address]."

Click on Go. This is the blue button located at the bottom right corner of the warning window. If supported by WINE, the EXE file will begin to run.
- If the EXE file does not show when using WINE, try the next method.
Use Boot Camp

Make sure you have the Windows installation file. The Boot Camp program on macOS supports Windows 8, 8.1, and 10.
- You can also download the Windows ISO file from the Microsoft website.

Open the Utilities folder on your Mac. You can do this by clicking the magnifying glass icon in the top right corner of your Mac screen, typing "Utilities", and selecting the Utilities folder.

Double-click on Boot Camp Assistant with the gray hard drive icon.

Follow the on-screen instructions. This includes selecting the Windows installation file, choosing the drive where you want to install Windows, and restarting your Mac.
- If you are installing Windows from a USB drive, you will be asked to plug in the USB during the process.

Wait for your Mac to restart. After the Boot Camp setup finishes, your Mac will prompt you to restart. Once your Mac reboots, you'll be directed to the Windows installation screen.

Select the "BOOTCAMP" partition if needed. If you're installing Windows from a USB drive, you'll need to select this option to proceed with the installation.
- If you're installing Windows directly from the ISO file, Boot Camp will partition the drive for you.

Follow the on-screen Windows installation instructions. This process may vary depending on the version of Windows you're using, but you'll need to restart your Mac after finishing, just like when you set up the Boot Camp Assistant.

Hold down the ⌥ Option key while your Mac restarts. This will launch the Startup Manager window.

Release the ⌥ Option key once the Startup Manager window appears. This window will display a variety of drives that you can choose from to restart your Mac.

Click on the "Boot Camp" icon, then press ⏎ Return. This action will launch the Windows operating system on your Mac.

Access and double-click on the EXE file. When using Windows, the EXE file will automatically run after you double-click it.