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iTunes and ID3 tags

Is there a way to automatically do this? I had never realized it doesn't update ID3 tags automatically. I could have sworn it did when I was testing it (I add 2.star/3.star/etc to the comments field).

But I just moved a lot of music off one computer for my mom, imported it... and boom, tags were not there.

Right clicking and doing convert ID3 tags works it seems, but it's quite frustrating.
 
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