Now this one was driving me up the wall. One of our users has a new Iconia Tablet and wasn't able to use the Android market at all while behind my firewall but worked fine everywhere else. I did a trace with TMG and there were no errors, all outgoing connections looked fine. So I went ahead and threw on Network Monitor onto the firewall so I could see where it was going. I noticed that 74.125.227.4 kept popping up which resolves to android.clients.google.com. I added that to the Web Browser tab for the proxy and then let the settings kick in and it fixed the problem. So I'm guessing that there's some issue with the TMG proxy and the google market.
Well, that didn't fully knock it out of the park. Apparently it also tries an outbound TCP 5228 which I also had to add to the protocol list for my users.
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