I found the upstream bug tracker and submitted this there, along with a patch to fix it. Hopefully this will make it into ubuntu before Natty.
** Bug watch added: freedesktop.org Bugzilla #32492 http://bugs.freedesktop.org/show_bug.cgi?id=32492 ** Also affects: media-player-info via http://bugs.freedesktop.org/show_bug.cgi?id=32492 Importance: Unknown Status: Unknown -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/685545 Title: Cannot transfer video files to iPod (Touch, 2nd gen) -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs