I think the error is 800xxxx something, right. I had the problem with almost all my tracks (amazon, itunes purchased as well as ripped, and podcasts). First solution was to update to Preview 2 of the Windows Phone app. Assuming you're on windows. Most songs transferred ok but still had problems with 2-3 songs and 4-5 podcasts, especially, Wait Wait Don't tell me. Only a few wouldn't sync.