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How to install iTunes 12 on Linux Mint 18 with working Store
Installer

Brief: Ubuntu is dropping 32-bit desktop images from the upcoming Ubuntu 17.10 release. This paves the road for killing 32-bit support entirely from future Ubuntu releases. Remember I told you about Ubuntu considering to drop 32-bit support in March this year? It seems the decision has been finally made.

iTunes12-Wine-Ubuntu.txt
Trying to run iTunes with Wine, i faced various problems. Here is a working solution how to install iTunes on Debian-based systems (in my case Linux Mint 18.1) - with support for the iTunes Store. Warning: Syncing i-devices is still not possible.
When installing it with the playonlinux-'iTunes 12'-script, log in into the Store was not possible in my case. Wine showed the follwing error when trying to log in: SecurityContext failed with error 0x80090304
1. Install current Wine version (2.0.1) directly from the winehq repository
wget -nc https://dl.winehq.org/wine-builds/Release.key
sudo apt-key add Release.key
sudo apt-add-repository 'deb https://dl.winehq.org/wine-builds/ubuntu/ xenial main'
sudo apt-get update
sudo apt-get install --install-recommends winehq-stable
wine --version
2. Create a new 32 bit wineprefix (if you are doing this on a 64 bit system) and set windows version
WINEPREFIX=/home/user/.wine32 WINEARCH=win32 wine wineboot
WINEPREFIX=/home/user/.wine32 WINEARCH=win32 wine winecfg
Set Windows Version to Windows 7 or newer
3. Download the newest winetricks
sudo apt-get remove winetricks
wget https://raw.githubusercontent.com/Winetricks/winetricks/master/src/winetricks
chmod +x winetricks
sudo mv -v winetricks /usr/local/bin
4. Install gdiplus library using winetricks
WINEPREFIX=/home/user/.wine32 winetricks
Standard wineprefix > install Windows DLL > gdiplus > OK
5. Download iTunes Version 12.1.3 - 32 bit and install it (version is important!)
https://support.apple.com/kb/dl1614?locale=de_DE
cd /home/user/Downloads
WINEPREFIX=/home/user/.wine32 wine iTunesSetup.exe
Follow the setup, anwer the AutoRun Question with NO.
6. Start it. It may crashes the first time, just start it again. Now you should be able to use iTunes and log in to the iTunes Store and download and play your purchased music and videos!
Start from command line:
cd /home/user/.wine32/drive_c/Program Files/iTunes/
WINEPREFIX='/home/user/.wine32' wine iTunes.exe

commented Jan 28, 2018

Thanks for the gist, I had a little trouble with this, but I managed to make it work from the info you gave.
The download wouldn't work (don't know why, but I normally use a proxy with wget, so the proxy may have interfered) for the gdiplus -- so I used wget to get the file and copied it to the location it wanted to find it.

$ wget --no-proxy -c https://download.microsoft.com/download/0/A/F/0AFB5316-3062-494A-AB78-7FB0D4461357/windows6.1-KB976932-X86.exe

$ cp -p windows6.1-KB976932-X86.exe ~/.cache/winetricks/win7sp1/windows6.1-KB976932-X86.exe

Once I did the cp -p of the downloaded file, I ran winetricks again and it found the downloaded file and did it's magic.

I also downloaded the latest 32 bit iTunesSetup.exe -- Help -> About iTunes won't show the version, but it was 12.7.3.46 (downloaded 32 bit iTunes as at 20180129).

2FA wouldn't work, so I disabled that and then I could login to iTunes okay.

Thank you!

commented Dec 2, 2018

This works for me, too. But as per @affinityv's reply, 2FA wouldn't work. But now turning 2FA off is not possible. Not sure if anyone has ran into a solution?

commented Dec 29, 2018

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commented Oct 28, 2019

I'm attempting to install a freshly-downloaded Windoze 64-bit iTunes on Linux 4.15.0-65-generic x86_64 These instructions got me farther than any other --- thanks! --- but I am still having some issues:

  • The iTunes UI comes almost entirely black; that's okay, since I don't need to actually do anything except..
  • ..I'm trying to restore a 64GB iPad to factory settings; I can't get iTunes running on Wine to 'see' the iPad.

Suggestions?

commented Nov 17, 2019

+1 here

commented Dec 25, 2019

Playonlinux itunes

I'm attempting to install a freshly-downloaded Windoze 64-bit iTunes on Linux 4.15.0-65-generic x86_64 These instructions got me farther than any other --- thanks! --- but I am still having some issues:

  • The iTunes UI comes almost entirely black; that's okay, since I don't need to actually do anything except..
  • ..I'm trying to restore a 64GB iPad to factory settings; I can't get iTunes running on Wine to 'see' the iPad.

Suggestions?

Apparently this only works with 32-bit iTunes.

commented Dec 26, 2019

@olyerickson
The black screen seems to appear on some Intel GPUs. Maybe the workaround described here works for you. Please also try iTunes 32 bit as @waynedmoore said. This should fix the black screen, but unfortunately I never got USB devices working in wine.

But: iPod, iPhone, iPad are definitely working if you install Windows+iTunes in a VM (VirtualBox) as described here.

Nevertheless (if you only want to reset your iPad) you should be able to do that through the system settings on the iPad itself.

There were also some attempts for USB passthrough in wine, but I haven't tested it yet. I’ll paste the link here so someone might try it out.
https://web.archive.org/web/20130527123059/http://wiki.winehq.org/USB

commented Jan 29, 2020

This pretty much works for me but I can't sign in to my apple account. It crashes every time the login dialog comes up. Speed.exe 1.3 v. Does anyone else experience this?

commented Feb 22, 2020

+1, dunno what seems to be the problem. I totally have no wish to install or even possibly re-instal with POL.

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