Transfer Purchases on iPod classic.

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Germansuplex

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I have one song that has mysteriously disappeared. An iTunes purchased track, to be precise. I'm not so much upset at losing the track as I am that my iPod did not prompt me that purchased content on the iPod was not in the library and about to be lost. The file is backed up to a disc somewhere, but I remember the 5G popping up the message that purchased content was about to be erased, but I could sync it back to iTunes first if I chose.

Is this one of the many bugs, or have I done something wrong, maybe missed a setting somewhere? I've tried the right-click, transfer purchase option. It was a no-go... too late, I'm guessing.
 
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