How to Sync iPod, iTunes and Virtualbox

VirtualBox is a Virtual Machine (VM) software originally created by Sun Microsystems, now owned by Oracle. It is possible to create a Windows VM using VirtualBox and install Apple's iTunes. This is typically done with versions of Linux, such as Ubuntu, which have no native mechanism to synchronize with iPods and iPhones. Apple has not written a version of iTunes for Linux, and so there exists no other simple method to sync files to an iPod on Linux computers.

Things You'll Need

• VirtualBox software package
• Windows XP service pack 2 or greater
• iTunes version 8 or 9
• iPod
• USB cable

Instructions

1. Install VirtualBox. If it is already installed, ensure you have the latest available version for your operating system. Upgrade if you are not current.

2. Create a New VM with Windows XP. Install Windows XP, and upgrade to a minimum of Service Pack 2.

3. Install iTunes in your Virtual Machine. Either iTunes version 8 or version 9 is confirmed to work.

4. Within the settings for the Windows VM, ensure both the "Enable USB Controller" and "Enable USB 2.0 (EHCI) Controller" boxes are checked.

5. Connect the iPod with a USB cable. Confirm that iTunes sees the iPod by looking for it in the left column of the iTunes window.

6. Sync the iPod in iTunes. Select the iPod in the left column of iTunes and then select "Sync" in the main window.

Tips & Warnings

• You can add a filter to VirtualBox to allow the iPod to automatically pass through, otherwise you will need to manually select and enable the iPod whenever it is plugged in.

• VirtualBox is known to be very sensitive regarding the USB devices management, and you may have additional operating system-specific configuration steps to enable USB device pass-through. Such steps depend upon the distribution of Linux you have installed.

References

• /dev/random: iPhone + iTunes + VirtualBox
• Ubuntu Community: Using iTunes via VirtualBox
• Mike's Blog: Ubuntu and iPhone4 Sync

Resources

• VirtualBox