I have noticed that all the songs in my iTunes library are not syncing to my iPhone, iPod Classic and iPad. For example, I have a Christmas playlist in iTunes that has 327 songs. Here is how the breakdown is for each device: iTunes (Windows 7 laptop) 327 songs iPod Classic (80GB-57GB free) 278 songs (49 songs missing) iPhone 4 (32 GB, 19GB free) 325 songs (2 songs missing) iPad (32GB, 12Gb Free) 325 songs (2 songs missing) iPhone 3G (8GB 3Gb free) 320 songs (7 songs missing) The example above is only for the Christmas playlist, but similar results are there for other playlists as well. I only have specific playlists synced with the iPhones and iPad where the entire music library should be on the iPod, yet that device has the greatest amount of missing songs. All devices were synced one right after the other in the order shown above. As for the iPod, which is set to sync all music, the iTunes library on the PC shows that there is 3696 songs and the iPod only shows 3259 songs, which means there are 437 songs missing from the iPod. I don't get it.