I think that there might be some slight gliches here. The first would be the duplicate file issue. It might be that for whatever reason, you have more than one of the same song in your library/ iPod and this might be giving you trouble. I have experienced something like this, as well. I just eliminated the duplicate and things were fine. I would check the settings in your account and check the desktop ipod settings to see if anything has changed between when you last synced and now. If this doesn't work, I would safely eject the iPod from the desktop/ laptop and then restart the machine. It might be a problem with the desktop and perhaps restarting would configure things properly. If you have not downloaded the newest version of iTunes, perhaps you might want to take a look at doing so. There are times when the new version of the program has an impact on whether or not you can sync. Namely, the more updated the program, the easier it is to sync. If these don't work, I would contact the customer service people. My experiences with them is that they are very receptive and are able to diagnose problems fairly well with iPods and challenges with them.