Not updating completely

My wife's iPod is not updating everything from the Library although it is set to update all playlists. What could be the reason for that? I resorted to manual operation to get around the problem, but strangely, it would let me drag only a small number of tracks at a time instead of all the missing ones at once. Another puzzle. Any theories.
I'm not sure this matters, but the tracks are from a Harry Potter audio-book CD set.
Thanks!

This is a bug in the Touch's handling of 'select by' filters in smart playlists. Search the forum for 'smart playlist', to see prior discussion on this topic.

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