This item does NOT work with the 2nd gen ishuffle (I did not try it w/ any other gen). Won't be recognized to sync or charge. Seller requires buyer to pay for return postage...even though this item is absolutely useless. I'm sure they do fine on this cheap piece of plastic, since most of us will not waste the return postage money.I'm using Win 7 64 bit.Should have known better- too many 1 star reviews to ignore!!!