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All the programs I use on my Mac these days are either in a Linux VM (in Virtualbox), or open-source apps which are also available on Linux. With one exception: iTunes, which I only use to feed my iPod Touch (4gen).

I'm tempted to switch over to Linux entirely, but I don't want to completely lose the ability to update/backup my iPod, and I don't want to deal with the hassle of dual-booting. (I can buy apps on my iPod itself, but apparently I can't download MP3s or subscribe to podcasts without using iTunes on a computer.)

I've heard that you can't run (non-server) Mac OS X in a virtual machine, even on Apple hardware. I do, however, have an old Windows XP license.

Is it possible to run iTunes 10, including iPod Touch (4gen) syncing, in a virtualized Windows XP on a Linux host? I've the most experience with Virtualbox (at work and home), but I'd be willing to entertain the possibility of switching to another VM.

I found this article that says it's possible, but is rather old: it only speaks of the iPod Touch 1gen. This other article has no date but mentions iTunes 8 (which Wikipedia says was shipped with the iPod Touch 2gen).

It doesn't need to be terribly convenient. If CD ripping doesn't work, for example, I'm happy to rip elsewhere and copy the files to Windows for iTunes. I really just want the ability to copy data onto my iPod, including iOS updates, and do backups.

Has anyone tried this more recently? Is it still possible with iTunes 10 / iPod Touch 4gen?

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Have you tried setting up an XP VM? iTunes runs fine on XP; your sticking point will be the USB support in your host OS and the virtualization environment. –  Adam Robinson Feb 8 '11 at 23:24
    
No, not for this. I figured I could potentially save a lot of time by asking if somebody else had done it first. –  Ken Feb 9 '11 at 0:40
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1 Answer

Is this possible? Legal? If so, what are the drawbacks and tricks

As of OS X Lion 10.7, the EULA permits you to use the OS in two virtual machines, on Apple hardware:

(iii) to install, use and run up to two (2) additional copies or instances of the Apple Software within virtual operating system environments on each Mac Computer you own or control that is already running the Apple Software.

This was first allowed with OS X Server 10.5, and both VMWare Fusion and Parallels Desktop allow you to easily setup an OS X guest machine, as does VirtualBox

An OS X guest on non-Apple hardware is possible with some fiddling, but is in violation of the software's EULA (i.e doing so is of questionable legality..)


iTunes, running in a VM, will be able to see the iPod/iPhone/iPad. As long as the USB can be connected to the VM. So this depends on which setup you are using. The above should explain the legalities of the OS X and VMs.

You can install Linux on Apple hardware, then run a VM of OS X (10.7 and above) on the machine to be able to use iTunes to keep the library in sync and updated, etc., and it won't cause you any issues.

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