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Thanksgiving Day tech support for Mom. She uses music playlists on her iPad for a class for special needs children, but one playlist is not fully

Syncing. There are 13 songs on a playlist. She wants 18. I added the songs in iTunes and synced and they are not on the iPad playlist. I added the songs to the playlist on the iPad and synchro and they disappear. The songs are on the iTunes playlist and they are downloaded to and playable on the iPad. I redid the entire playlist from scratch and the same 5 songs do not sync. I cannot figure out why.

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