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I don't know if this helps, but I can't get my 30GB 5th generation iPod classic to work with my 2010 radio either. The same thing happens.
I'm using a amazon.com cheapie USB/3.5mm jack, but I don't think that is the problem.
I haven't tested this theory yet, but my iPod classic is formatted HFS+ (Apple) and not FAT (Windows).
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