I have a new iPod Touch (4th gen), and am using the new iTunes 10.0.1. I'm not sure which is actually causing the problem. Whenever I have the "Convert higher bit rate songs to 128 Kbps AAC" flag checked, iTunes will crash randomly ("iTunes has quit unexpectedly...") after syncing some tracks. A few times it went many hours (it takes over 24 hours to sync the whole iPod), but once it starts crashing it starts doing it after only a few tracks. The iPod will sync happily when the "Convert" flag is not checked. This function worked correctly with my old iPod (5.5gen) and iTunes 9. I tried all the usual fixes-- reinstalled iTunes, reset the iPod to factory settings and restarted the sync, trashed iTunes' preferences, etc. It isn't any one particular bad track (I tried that). When iTunes 10.0.1 came out I hoped they would have fixed the bug, but no joy. I spoke to Apple and they basically said "Wow, that sounds like a serious bug" and suggested I look into 3rd party software (which they wouldn't name). A bit of googling suggests others have had this problem, but no solution, and I'm not sure if ANYONE has gotten this function to work in iTunes 10. Any ideas or workarounds?