In iTunes I have a Smart Playlist that lists my 30 most recently added songs, which I use frequently to play my latest music, quite handy when I find a new song I like but maybe forget the artist or what not. When I sync my iPod touch, this playlist shows up, but instead of showing the 30 latest songs added, it shows the first 30 songs alphabetically (which happens to be 30 Seconds to Mars). I've tried to delete this playlist, re-create it and then re-sync it, but it still messes up. It's done this through multiple updates and restores, jailbreaks and clean firmwares. Currently my iPod (2g, 32gb, not preloaded with 3,1) is running a jailbroken 3.1.1. It did this when I ran 3.1 un-jailbroke, 3.0 both jailbroken and not. If it matters I am running Snow Leopard, not Windows.