Artwork + info not being updated from itunes.

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Hi, any help with this would be appreciated. Apologies in advance if there's a really obvious answer to this.

I originally transfared all my music to my ipod nano (4th gen) with itunes without alot of the artwork. Since then I've gotten all the missing artwork onto itunes manually. Now, when I hook-up the ipod and transfare new music, also hoping that the missing artwork would be updated automatically and appear on the ipod also, it's still missing, despite being there in my itunes library.

I'm syncing my music manually btw, since I don't want my whole library on my ipod.

I'm really hoping I'm not going to have to delete everthing and sync again (oh, to be a anal retentive perfectionist), but there has to be a way around this!
 
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I had the same problem, also with the wrong artwork appearing on the tracks.

Only way I find is to clear out your playlists and sync up so that the ipod is cleared down, then re build your playlist(s) and re sync.

At one point during my faffing around and trying to sort this I restored my nano back to factory and re synced everything

Yes it takes times but this I have found is the best way
 

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