Hi, Out of all the iPods my family has owned (dating back to 3G...), this is the first time I have a problem. Although it may be an iTunes problem. I have these uni. lectures (around an hour each, they're audio files) that I want to put on my iPod. I successfully converted them to AAC, and they're on the iPod and play fine. I want to organize them into playlists though. For example, I want one playlist to say "A" with maybe 5 lectures, then another playlist "B" with another 5 lectures, etc. From what I've told - this can be done by clicking the little plus sign to make a new playlist, rename it, and simply drag and drop. Simple, right? Well, once I sync it, for some reason, although the playlist shows up on the iPod, only the first lecture is there! I added 5 lectures to the playlist on my Mac, then when I sync, it only adds the playlist with the 1st lecture! The other lectures I added to the same playlist on my Mac aren't on the playlist in the iPod. If it helps, it's a 5 G iPod, and I'm running OS X with all updates. For the record, I tested this on 2 iPods (5G) and the same thing happened. I restored one of the iPods to see if it would work, and it didn't. Any help will be much appreciated. Thanks!