Trying to sync my iPad with the iTunes library I have running in a VirtualBox virtual machine kept failing. I’d get spurious “error -5000″ messages or simply that it had failed to start. Further investigation brought to light the strange fact that I couldn’t even play any files and podcasts would download but fail to be added to the library. Trying to play the files using the built in network sharing to other iTunes clients would fail too.

What could be causing it?

End tasking and even a reboot didn’t cure things. I began to wonder if it was a change in iTunes itself, maybe Apple had disabled the use of a mapped drive for your library. Can’t be, things stopped working some days after I had updated iTunes. I then thought about the fact that the drive mapping was via the shared folders within VirtualBox rather than a straight up CIFS mapping. More recently, I had updated VirtualBox itself, maybe I forgot to update the virtual tools too? Could that be causing it?

One install and reboot later and iTunes is behaving itself! So, if you have the same problem I’d recommend ensuring your version of the virtual tools installed in the guest OS matches the version of VirtualBox you are powering it with.

 

Problem solved, podcasts synced and a smile brought back to my face :)