Hello, I have exactly the same problem w/my nanon 7th gen and also had this problem w/my nano 6th gen. Very frustrating. I've probably spent 4 hours trying various tricks to get it to work and nothing has helped. Spent an hour on the phone w/Apple tech support and they were worthless - neither of the techs I spoke to had a clue how the uploading should work, they were both just reading from a script. I had/have a far better understanding of the issue than they do. Nike was more knowledgable but still couldn't help. At least he volunteered to enter a help ticket w/his tech team. Said that he never saw any data come across despite trying multiple uploads while on the phone. I suspect itunes is the issue - it never asks for my Nike ID so how can it possibly know where to send the data?! I patiently explained this to the Apple reps multiple times but they never seemed to get it. In the end they just claimed everything was working from their end (how do they know?) and blamed it on Nike. Very dissapointed in Apple.