i had the same problem with NW-HD3. i eventually noticed that the tracks that skipped were the ATRAC ones. it didn't seem to matter what bitrate i used either. however, anything transferred as an MP3 was fine. so, once again, a whole bunch of music had to come off and go back on again. if i were to upgrade to SS 4.0 would i have to re-initialize my player? it would only be the third time this year...