I was wondering if anyone can help me out with this. I have a 4GB Nano (which is scuffed up beyond belief... but I still love it). It's pretty much full to capacity (maybe 100MB free). I listen to quite a few Podcasts on my commute to work. I have iTunes set up to keep only Podcasts I haven't yet listened to. My problem is that iTunes wants to put the new content on my Nano before it removes the stuff I've listened to... and as a result, I get the message saying that I don't have enough room and "Would you like iTunes to make a selection of music to copy to your Nano?". If it would remove the content I had already listened to first, there would be plenty of room. For now, I've set iTunes to only keep the most current Podcast. This kinda sucks because I don't always get a chance to listen to all of them. Is there some way to get iTunes to remove my old content before trying to copy over the new stuff? I know I can do it manually, but that's sort of a pain (one of the biggest reasons I still use my iPod is because of the integration with iTunes and syncing up my Podcasts). I'm guessing there's probably not much I can do... but since I don't really play around with any settings in iTunes or my Nano, I thought maybe I missed something.