On my setup on Windows it loads the playlists fine, the newest first in Itunes 9 itself but dis-ordered on my ipods. On the Ipod touch v1 with 3.1.1 Firmware I can't fathom how it's sorted, it's totally scrambled the order but on the Ipod Classic V1 160Gb it appears to be sorted via artist. Even if you re-sort it by clicking the date added column the order of the playlist and resync it makes no difference to either of them. Neither does deselecting, resyncing, unplugging -replugging adding back and syncing again. Anyone else have this issue or am I in the minority of one? EDIT: Looking at the Apple Support Forums it seems like Smart Playlists are broken for many users on both Windows and Mac. Itunes 9.01 will be on it's way shortly!