First, make sure that your Chromebook has Linux enabled. If you plan on purchasing CrossOver for your Chromebook, it will cost you a one-time fee of $14.99. Now, if you feel like you rent someone who wants to deal with typing out Linux commands and don’t mind paying a small amount for software that is an alternative to Wine, then CrossOver is the program you need. RUN EXE Files on Chromebook Using CrossOver EXE file to run and install the program on your Chromebook. Once you have done that, simply double-click on the. Make sure to name the EXE file in a single word with no spaces (example.exe). Now that you have Wine installed on your Chromebook, simply copy the exe file that you wish to run or install on your Chromebook. And finally, type in sudo apt update to update the Wine app. You will now see Wine being installed on your Chromebook. Now, type in $ sudo wget -nc -O /usr/share/keyrings/winehq-archive.key and finally hit the enter key. Type in sudo dpkg -add-architecture i386 and run the command. With the Terminal app opened, it’s time to enter in command to install Wine on your Chromebook. Here are the steps that you need to follow in order to install Wine on your Chromebook. Now that you have enabled Linux on your Chromebook, you are only a few steps away from running the EXE files on your Chromebook. Your Chromebook will now be having a Debian 10 (Linux environment) where you can enter Linux commands. This whole process can take under 10 minutes. There will be a few instructions you will have to follow. Click on the option to enable or turn the feature on. 
You should see an option that says Linux Development Environment.Now, click on the Settings icon followed by Advanced.Power up your Chromebook and click on the clock present at the bottom right of the screen.You can follow these steps to enable Linux on your Chromebook to install Wine. Since Wine is a Linux application, you would first need to enable Linux on your Chromebook. Now, let’s take a look at how you can install Wine on a Chromebook in order to run exe files. Wine is not a Windows emulator as it translates Windows API calls into POSIX calls right away. Wine is a compatibility layer that allows you to install and run exe files of windows programs.
In order to run EXE files on your Chromebook, you will have to make use of Wine.
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