I usually sync one of my playlists by Date Added (newest to oldest). But since upgrading to iOS 5 on my iPhone, no matter how I set it on my iTunes it only syncs the playlist as Oldest to Newest. If I arrange my playlist by artist on iTunes then it follows that but when I switch it back to Date Added it only goes oldest to newest & not the other way around. A very weird issue. Also to note I don't have the same issue with my iPad which also has iOS 5. Both syncing on the same Mac.