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On a number of occasions I have synced my iPod after several months of ratings only to have all of my meticulously applied stars get erased from the iPod Classic.

I switched from the more convenient Manual mode to Automatic management but it still seems to wipe my ratings. The ideal behavior would be to have iTunes sync the new stars back to my library. Why wouldn't this happen?

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Im not sure this is default behavior. I use stars and smart playlists to actually help manage things (smart playlist to delete songs, and then rate things with 5 stars that need to be 'processed'). I sync usually once a week, and it always syncs these changes back and forth.

Its supposed to sync all the songs in recently played to update their metadata (like playcounts) as well. Maybe if you don't sync for months, that playlist doesn't show everything, and therefore looses some of your ratings?

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Ah hah, maybe that is it-- it only syncs the recently played! That would explain my experience if so. Thanks. –  thadk Sep 24 '10 at 2:43
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you may be able to get around this by adjusting the smart playlist of recently played (tell it to show more than a month for example). –  jmlumpkin Sep 24 '10 at 14:09
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