My Server 2008 R2 Std box will not run windows updates if I am going thru my web proxy (Mcafee Web Gateway 7v). I keeps prompting for a username and password and even if you supply the UN and PW it still doesn't work. It appears that Server 2008 R2 doesn't handle intergrated NTLM proxy authentication. This is issue is only with windows updates. I can get to the Internet. I have tried the solutions in: Problems in proxy Authentication (SOLVED) http://social.technet.microsoft.com/Forums/en/w7itpronetworking/thread/632c4368-cad1-47df-846f-3f15bc34c8b4