From Wired: iPod Shuffle's Vanishing Music
I've been pretty proud of my 2nd-gen iPod Shuffle. It looks great, it weighs nothing and it clips on my shirt-tail. But it also ate a few dozen of my favorite songs from iTunes, and I can't find a culprit. Is it a new bug or an existing problem?
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I don't know where the songs went but I am willing to bet they went to the same place as the missing sock from the dryer.
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