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it's a couple of days that I'm experiencing a strange problem: I have an iPod Touch 4 that I used to sync with my iTunes library. The problem that I'm facing is that, somehow, the synchronization fails.

What happens, in details, is that each time I try to sync iTunes goes through 3 steps: a backup copy, a preparation for the synchronization (as usual), then it detects a group of songs (that should have already been synced) as new tracks, add them and synchronize. Notice that the synchronization appear successful according to iTunes.

And this is the first problem. Why it keeps detecting those tracks as new? Besides, the songs are actually on the iPod (I can play them).

The second problem is that most of album covers do not correspond to the correct album. And this is bad. Also because if I check in the iTunes library they are correctly set.

I'm using iTunes 10 on MacOSX 10.8, the iPod has iOS 4.1. I know the iOS version is pretty old, but I have my reasons to keep it, and really do prefer to keep it and not to update unless absolutely unavoidable.

Any suggestions?

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Why aren’t you upgrading to iOS 6? Perhaps we could help you with it if you tell us the reason. –  duci9y Oct 4 '12 at 7:54
I don't see how this is important, however I'm a developer so I need my iPod to remain old in order to provide compatibility with older version of iOS. –  Saphrosit Oct 4 '12 at 8:51
Apple’s guidelines state that you shouldn’t support versions older than iOS 5. Did you update to iTunes 10.7? Perhaps something changed in it which affected iOS 4 syncing? There are not many people on iOS 4, so it will be difficult to find other people with the same problem. –  duci9y Oct 4 '12 at 8:58

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