A couple of weeks ago I downloaded an album with iTunes and proceeded to sync it with my two iPods. I recently skimmed through my playlists on my iPod, I noticed some albums had completely disappeared and other playlists had some some of their content removed. I called Apple and even though the rep was very helpful, he couldn't understand why that happened other than the fact that my iPods were 2nd generation and the newest iPods were 6th generation. Part of the problem might also be a lot of my songs on my iPod I copied from CDs and since Apple has now joined the streaming crowd, iTunes has been adjusted not to recognize songs not downloaded from Apple. So, if anyone has iPods which haven't been synced in a long time and have music not purchased from Apple, they might be wise not to do so since the latest updates.