Not sure if it was just until 2009. This seems related, and it's dated Sep 2013:
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After both updates (iTunes 11.1 and ios 7) everything was fine for a few days. Yesterday however I noticed my iPod was skipping songs as I had it on 'shuffle', most of them just wouldn't play. I tried selecting these songs from my iPod but the text was grey instead of the usual black colour. There were also squares next to these songs with circles around them.
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and
Quote:
I do not purchase music from iTunes. I buy CD's, download music using codes provided when I buy Vinyl records or download free music online.
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https://discussions.apple.com/thread/5368528