Let me begin by qualifying that I have the 32GB 3GS with latest OS & iTunes updates. So the simple problem I have is that the smart playlist does not update songs on the iPhone. My playlists are organized from "least recently" played. I know that with my Nano, when I finish playing a song from one of these smart playlists, the song is removed as it no longer fits the criteria. However, the smart playlists on the Iphone does not do this. I did an extensive search on this topic and can't seem to find a solution.