Syncing an iPod Nano with Windows under VirtualBox in Ubuntu

I bought an iPod Nano (7th generation) for my son, and decided I wanted to use a Windows 7 virtual machine to house the iTunes software necessary to manage the gizmo. Apple items need to be managed with iTunes running on a Windows or Apple computer (there are options for dealing with iProducts from Linux, but since this is my son's gizmo I don't want to have to deal with them). I have been using Linux on my desktop and laptop for some time now, and the only things I use that have to run on Windows (for which I created the VM) are some tax software and the sync software for the Fitbit. And now this.

Since tax season is past and since my Fitbit split apart into a kazillion pieces, I have had little need to run the VM, so the first problem I had to deal with was the excessive number of Windows updates to be sifted through. Once that was done, installing iTunes was easy but connecting to the iPod was unsuccessful. Windows kept telling me that it could not start the device, could not find the device, could not find the appropriate driver, etc. It turns out that the problem was USB 2.0 compatibility--the iPod quietly requires USB2.0 and the current version of VirtualBox doesn't support it directly. Instead of going through the whole troubleshooting story, which would bore you to tears, I will just cut to the chase and tell you the things I did to get it running properly.


The core of the problem, as I said before, is USB2.0 support. To enable USB2.0 support on VirtualBox, I needed the "VirtualBox Extension Pack." But the extension pack is available for version 4.2.12, and the version in the Ubuntu repositories is 4.2.10. So to get everything working, I did the following:

First, replace my existing VirtualBox installation with version 4.2.12:

• Uninstall VirtualBox with sudo apt-get remove virtualbox (this doesn't remove any of my virtual machines--just the virtualbox application)
• Download version 4.2.12 (or whatever the latest version that has a compatible extension pack is) from the VirtualBox download page.
• Download the extension pack from the same page
• From the file manager, double-click the .deb file to install the application (if it notifies about conflicts from something installed with the old version, just uninstall the conflicting package and let it be installed with the new version of VirtualBox).
• From the file manager, right-click the extension pack file and select Open With Other Application, then choose Virtualbox
• In the virtualbox application, before starting the VM, select the USB section and set the checkboxes for USB 2.0 compatibility.

Next I wanted to make sure that the VM always grabs the iPod and pushes it to the VM's USB devices:

• Plug in the iPod so it is present in the list of USB objects
• In the USB section of VirtualBox as above, click on the icon for Add Filter from a Device (the second one, with the green plus), then select the iPod device from the list
• Click OK

I then started up the VM and pluged in the iPod, and (since I had already installed iTunes) the iPod was recognized and usable within the VM.