HT1351 Songs won't sync properly and I don't know how to fix it. Help!

I keep trying to sync my music to my iPhone but some of the songs aren't uploading properly and when trying to listen to them, my phone will just skip over them and they won't play. When looking at the songs on my playlists they show up as gray and there is a red square with a circle around it like it is syncing. Also iTunes won't sync any of my playlists anymore even though it says, on my iTunes account, that they are uploaded to my phone. What should I do?

I have the same issue: my playlists are not showing up on my iphone. The old playlist are there and the music is there but the playlists will not update. I'm hoping someone has an answer?

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