How to Install iTunes on Chromebook in 2020

How to Install iTunes on Chromebook

I’m sure you guys know what a Chromebook is, and that it’s very very popular. 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 some of the best Windows 10 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 on Chromebook 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? Well, we have used some of the best Chromebooks out there, and 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. However, if you’re interested, you can check out our guide on using iPhones with Linux.

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 some other apps like iTunes instead.

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. Meanwhile, you can take a look at some of the best Chrome OS tips and tricks to get the most out of your Chromebook.

59 Comments

  1. Beebom, Arjun,

    Either you have an adequate, reliable solution – or you don’t. This is a pedantic waste of time.

    My first visit to Beebom, and will be my last.

  2. Anyone have any idea to get Linux on a Chromebook that doesn’t have the “Linux (Beta)” Option in settings?

    Or how to update an older chromebook after Google stops supporting and pushing out the new OS to your Chromebook?

    Also, I know the writer needs to make money, but the amount of, and the intrusive placement of ads on this page, makes me not want to spend hardly any time at all on it. I feel like you would make more income from the ads by having less intrusive ads that might increase your page viewtime. Just a thought and some feedback. The amount of ads so much that they affect load time and my view of the content, literally makes me insta-back out of the page regardless of the information I think is on it. Because if the info was valuable…you’d make money mainly from page views…NOT from serving 50 ads per person viewing the page… smh

  3. I had the same problem. iTunes wouldn’t install, an error for Windows 10 and after that an error with the itunes.exe program. What I did was open Wine and change Windows 7 to Windows 10; then I used the iTunes 32-bit install from iTunes’ website and renamed the file itunes2.exe to type it easier. Hope this helps those who’ve seen this!

  4. so everything works, but when the iTunes window shows up, it says I have to be running Windows 10.

    1. yes, i have wine correctly installed. the result im getting is the san eone i get if i type in sudo apt-get install itunes

  5. Ok so the problem we are all having is that there are important steps missing like INSTALLING WINE!

    (after step 4)
    sudo apt-get install Wine
    sudo dpkg –add-architecture i386
    sudo apt update
    sudo apt-get install wine32
    WINEARCH=win32 WINEPREFIX=/home/username/.wine32/ wine itunes.exe

    That should work. Sorry if it doesn’t.

  6. I did all the steps and everything went smoothly but for some reason iTunes wont open in the end even after i had no problem installing it, the app wont open which is very annoying since i have spent 2 hours setting up Wine and iTunes

  7. WINEARCH=win32 WINEPREFIX=/home/yourusername/.wine32 winecfg wont work for some reason its giving me “command not found”

  8. I’m sorry but this attempted way to get your chrome book to do everything is a thankless task. For crissakes, a Win 10 computer can cost $250 and if you get a external or network hard drive you can do just fine. As soon as I see apt -get I run the other direction.

  9. i just spent two hours trying to download this, did everything right and it still just didnt work. and then i read the end XD this has to be a jokee

  10. 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?

  11. 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?

  12. 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

    1. its because you did not the get the iTunes install file from apple’s website so thats why

      1. 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.

  13. 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!!!

  14. 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.

    1. how did you change the instructions to make it work? I have a Pixelbook as well and am struggling with this.

  15. How do I download iTunes without damaging my ASUS C302C laptop? I’m wary of damaging anything on it.

  16. 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

  17. 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

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

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

  19. I have tried to set this up 3 different time. But it will not allow me to open the app at all.

  20. 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

  21. i am stuck on step 4, it keeps saying command not found, i typed in my username correctly??????

  22. 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

  23. It says “no such file or directory”, so stuck on step 4. Why aren’t y’all responding to comments?

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

  24. 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!

  25. 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 ” root@penguin:/home/xxxx# wine: ‘/home/xxxx’ is not owned by you, refusing to create a configuration directory there”

    What the heck am I doing wrong?

  26. 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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