AFAIK, the problem is that WindowsUpdate does not obey Internet Explorer proxy definition and tryies to connect directly (via default gateway definition at local station).
My solutions:
- allow direct connections at your firewall/default_gateway to M$ WindowsUpdate servers (there are many, maybe due to load sharing). I did this, it is not nice, but it works.
- implement transparent proxy at your firewall/default_gateway.



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