While the majority of American classrooms are filled with Chromebooks, it’s equally true that many users prefer the iPhone as their primary device. And eventually, that leads to incompatibility between two distinct ecosystems created by Google and Apple. Yes, I am talking about running iTunes on Chromebook and how you can get it working. Well, in this article, I bring you a detailed guide on how to install iTunes on Chromebook. We will also discuss the performance of iTunes on Chromebooks so you know what to expect from the app.

Install iTunes on Chromebook in 2021

Here, we have explained how to get iTunes working on your Chromebook thoroughly. To give you an overview, we are using the Wine app which is popular for running Windows apps on Linux systems. In tandem, we will install the Windows version of iTunes on our Chromebook through the Linux container. Now having said all of that, let’s go through the steps without further delay.

Run iTunes on Chromebook

1. First and foremost, you need to enable Linux and then set up Wine on your Chromebook. We have written detailed guides separately so follow the above-linked articles and you will be all set for the next step.

Install iTunes on Chromebook 1

2. Now, let’s go ahead and download iTunes for Chromebook. Keep in mind, the 64-bit version app does not work properly on Chromebook and displays a black window. I tested both the latest 64-bit and 32-bit build of iTunes (Dec 7, 2020) but the black screen issue is still there. So, you need to download this specific 32-bit version of iTunes from here. The build is 12.9.3 from August, 2019.

3. Next, rename the file to something easier like “itunes.exe” and move it to the Linux section.

itunes

4. Now, open the Linux Terminal and run the below command to update Linux to the latest build.

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

update linux

4. Having done that, open the Terminal and execute the below command to change the Wine architecture to 32-bit. Make sure to change yourusername to the actual username assigned to your Chromebook. To find the username, look for the portion before @penguin in 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 winecfg

Install iTunes on Chromebook 4

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

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

chrome os

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

Install iTunes on Chromebook 3

Create Shortcut for iTunes 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 and enable “Show Hidden Files”.

Create Shortcut for iTunes on Chromebook

2. Now, navigate to the following path: .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 from here.

Create Shortcut for iTunes on Chromebook 2

3. Having done that, copy the below path and paste it just after Exec= . Keep in mind, do change yourusername to the actual one.

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

Create Shortcut for iTunes on Chromebook 3

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.

itunes running on chromebook

My Experience with iTunes on Chromebook

While I managed to install and run iTunes on Chromebook, the question remains, does it work well? In our testing, iTunes did not perform well despite running on a powerful (i5, 8th-Gen) Chromebook. It’s quite expected as you are running iTunes inside a Windows container which in turn, is running inside a Linux container.

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 iDevices.

Our Experience with iTunes on a Chromebook

Having said all of that, the most disappointing part is that iTunes 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 other options.

Take a Look at iTunes for Chromebook

So that is how you can get iTunes on your Chromebook. While the installation process is not that simple, you can definitely try it on your device. Once you have set up Wine, the process becomes a breeze. Apart from that, on the performance front, iTunes didn’t work well but do give it a shot and see how well it fares on your Chromebook.

Anyway, that is all from us. If you are facing some trouble while making it work, do comment down and let us know the issue. We will definitely take a look. And whenever we find a proper build of iTunes working successfully on Chromebooks, we will definitely let you know.

To get the most out of your Chromebook don’t forget to read our Chrome OS tips and tricks article. Also, check out how you can play latest games like Among Us on Chromebook.

40 COMMENTS

  1. I’m on the second part, on the last step to download itunes and everytime i enter the last command: WINEARCH=win32 WINEPREFIX=/home/dlecrone12/.wine32/ wine itunes.exe, this is what it says,
    “0009:err:module:__wine_process_init L”C:\\windows\\system32\\itunes.exe” not found”
    What do i do?

  2. I have iTunes installed and it opens. However I cannot log in. It seems as though my Linux apps aren’t connecting to the internet. Any suggestions?

  3. when I enter the “WINEARCH=win32 WINEPREFIX=/home/username/.wine32/ wine itunes.exe” command, it only replies with
    0009:err:module:map_image Could not map section .rsrc, file probably truncated
    0010:err:module:map_image Could not map section .rsrc, file probably truncated
    0010:err:module:__wine_process_init L”Z:\\home\\username\\itunes.exe” not supported on this system

      • Thanks! I was confused on why I kept getting the 3 error messages but your reply helped me get past it. However, when you launch the window that appears right after this, it tells you that iTunes needs to be on the Windows 10 version, in which I believe has something to do with Wine. When you install Wine, you have these options on I think what Windows you install it on, I don’t know how to explain it. I’ll see what happens when I change it to Windows 10 and then retry.

  4. Why would anyone even try installing this? Itunes still doesn’t work on Chromebook. It says so in the description! Why would you install the wrong engine in a car? It won’t run! BAD ADVICE!!!

  5. This method didn’t work for me. (I have a Google Pixelbook). However, I adapted from the given method. I guess there were a few missing instructions and now it’s working.

  6. when i type the 5th command in it says “000f:err:service:process_send_command receiving command result timed out
    win: Bad EXE format for Z:\home\XXXXXXXXX\itunes.exe

  7. Hi Thought my prayers had been answered. I did get it working on acer chrome book but as you have said crashes and does not pick up my phone. Wished I had read to the end of the piece.
    That being said thanks for the experience on chromebooks they have a way to go

  8. Everything goes great until I do the one with “Itunes.exe” it says

    wine: Bad EXE format for Z:\home\user\itunes.exe.

  9. Can i get some help uninstalling it? i have no idea how it may be called ive read my dpkg –list lots of time and just cant find it

  10. I managed to get it installed, but what do I do after that? It doesn’t show up in my apps even after doing the shortcut steps

    • may be you havent create a directory correctly , i suggest doing it again and say the error message a bit more specificly

  11. So I installed linux and itunes, get to step 5, and type in the command WINEPREFIX=/home/yourusername/.wine32 change my username as suggested in step 5 but it just won’t let me go ant further. What am I doing wrong? SOS!

  12. So I get to the install iTunes part, step 5, and type the command ” WINEARCH=win32 WINEPREFIX=/home/yourusername/.wine32/ wine itunes.exe ”
    and it comes back and says ” [email protected]:/home/xxxx# wine: ‘/home/xxxx’ is not owned by you, refusing to create a configuration directory there”

    What the heck am I doing wrong?

  13. Long time I was wanted to install iTunes on my Chromebook. Unfortunately,every time i was fail.
    I didn’t understand my mistakes and didn’t know the trick to install iTunes. After all,my luck, i am here and reads this article. Thank you.

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