Not sure if it just me, but i made a Smart Playlist with all the songs of two artists which amounts to 40.56GB, i plug in my iPod Shuffle (2GB) and it says over capacity by 19.9GB which is fair enough (it's not 38.67 because i checked the convert to 128kbps AAC) so i checked, assuming this would fix it, 'Automatically fill free space with songs' because for some reason iTunes no longer gives me the option to fill iPod with a random song selection (like it used to) and nothing works, it doesn't attempt to sync any song from the playlist at all, can anyone help lol?