itunes 10 bug with syncing playlists
OS: Windows 7 Pro 64-bit
Itunes 10.0 and 10.1
I installed itunes 10 about a month ago loaded my library and everything was fine. Since then, I've noticed songs missing from some of my playlists. At first it was just a random song here and there and just figured I must have deleted the song from the list and forgot I did that. Then I started noticing more and more songs missing from the playlists that I know should be there. I checked my itunes library to verifiy the missing songs were on the playlist, they were. When I synced my ipod, the songs were missing on my playlist on the ipod. I could still find the song on my ipod by looking under albums or artist, but they were not syncing for the playlist. Song was checked to be synced, no errors at sync. The songs all played in itunes just fine, file corruption wasn't the cause. Only thing the songs that wouldn't sync had in common was that they were all purchased from the itunes store.
I was on itunes 10.0 at the time, so I upgraded to 10.1, same issue. Tried deleting and recreating the playlist, same issue. Deleted the songs that weren't syncing and restored them from my backup, same issue. Finally I just wiped by whole itunes library and readded all my music, then recreated the playlist, same issue.
Running out of options I decided to rollback to itunes 9.2. Had to wipe my library again, and readd everything. After reloading my library into itunes 9 I recreated my playlists and synced with my ipod. All playlists synced on my ipod correctly.