How to Install iTunes on Chromebook

You guys are probably aware of what a Chromebook is and how popular it is. While Chromebooks predominate in American classrooms, many users still prefer to use their iPhone as their primary device. And eventually, that causes the two distinctive ecosystems that Google and Apple each created to be incompatible. Yes, I’m referring to using iTunes on a Chromebook and how to set it up. I’ll give you a thorough tutorial on how to install iTunes on a Chromebook in this article. In order for you to know what to anticipate from the app, we will also talk about how well iTunes performs on Chromebooks.

Install iTunes on Chromebook in 2022

Here, we go into great detail on how to set up iTunes on your Chromebook. We are using the Wine app, which is well-known for running some of the best Windows 10 apps on Linux systems, to give you an overview. On our Chromebook, we will simultaneously install iTunes for Windows using the Linux container. After having said all of that, let’s begin the process right away.

Run iTunes on Chromebook

1. Prior to installing Wine on your Chromebook, you must first enable Linux on your Chromebook. Following the articles above that are linked to our detailed guides will have you prepared for the next step.

2. Let’s get started downloading iTunes for Chromebooks now. Remember that the app’s 64-bit version does not function correctly on Chromebooks and shows a black window. I tried the most recent 64-bit and 32-bit builds of iTunes, but the problem with the black screen persisted. So, you need to download this specific32-bit version of iTunesfrom here. The build is 12.9.3 from August, 2019.

3. Next,rename the file to something easierlike itunes.exe and move it to the Linux section.

4. Now, open the Linux Terminal and run the below command toupdate Linuxto the latest build.

sudo apt-get update && sudo apt-get upgrade -y

4. Having done that, open the Terminal and execute the below command to change the Wine architecture to 32-bit.

WINEARCH=win32 WINEPREFIX=/home/yourusername/.wine32 winecfg

Make sure to changeyourusernameto the actual usernameassigned to your Chromebook. To find the username, look for the portion before@penguinin the Linux Terminal. That s your username. Meanwhile, if a Wine window opens up, click on the OK button.

WINEARCH=win32 WINEPREFIX=/home/yourusername/.wine32/wine itunes.exe

5. Next, run the below command toinstall the 32-bit version of iTuneson Chromebook. Again, make sure to change your username. Instantly, an installation window will open up. Click on Next and proceed with the setup.

Create Shortcut for iTunes on Chromebook

6. After the installation, click on Finish and voila, there you have it. iTunes successfully running on Chromebook.

You have successfully installed iTunes on Chromebook and a shortcut has also been created in the App Drawer inside the Linux folder. However, when you click on it,the shortcut does not open iTunes due to an incorrect file path. So to fix this issue, follow these steps.

1. Open the native Files app and move to the Linux section. Here, click on the 3-dot menu andenable Show Hidden Files.

2. Now, navigate to the following path:

env WINEPREFIX="/home/yourusername/.wine32" wine "/home/yourusername/.wine32/drive_c/Program Files/iTunes/iTunes.exe"

.local -> share -> applications -> wine -> Program Files -> iTunes. Here, you will find iTunes.desktop file which is the shortcut that we need to edit. So, right-click on it and select Open With . Here, choose the Text app to open the file. In case, you don t have the Text app, install it fromhere.

My Experience with iTunes on Chromebook

3. Having done that, copy the below path andpaste it just afterExec=. Keep in mind, do changeyourusernameto the actual one.

4. Now, save the file and close the Text app. Finally, open iTunes from the App Drawer, and this time, it should launch perfectly fine. You can further pin iTunes to Chrome Shelf as well.

While I managed to install and run iTunes on Chromebook, the question remains, does it work well? Well, we have used some of thebest Chromebooks out there, and in our testing, iTunes did not perform well despite running on a powerful Chromebook. It s quite expected as you are running iTunes inside a Windows container which in turn, is running inside a Linux container.

Use iTunes on Chrome OS with Ease

So,the performance takes a hit significantly. Further, despite Linux gaining USB support on Chrome OS, iTunes was unable to detect iPhone and could not sync the library. Partly, it s because Apple does not officially support Linux connectivity for its devices. However, if you re interested, you can check out our guide onusing iPhones with Linux.

Having said all of that, the most disappointing part is thatiTunes crashes every time you try to sign in to your account. So, neither you can access your media library locally nor through the cloud. All in all, iTunes on Chromebook is not a good experience and you should look for some otherapps like iTunesinstead.