What do the logs at the proxy contain and look at the logs on the winblows server
I don't believe this is the place to further discuss if you do have a 2010 server config issue but from passed experience, make sure the 2010 server is configured to accept the connections (iis)
If that checks ok, you might look at the logs on your firewall/router to see what the connection is doing. Especially if you had separate LAN's
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