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Huh... the 2G Touch is the same jack as the iPhone 3G and I use mine all the time... hmmmmm
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I have my Touch in a Switcheasy Rebel Touch case, which I love (really protects the machine), and that could be the problem. The base of the W3 plug is round and fat, and while it may sit flush in the Touch without the case, the rim around the plug from the case input prevents the W3 plug from going all the way in.
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