If you wish to configure Windows 2008 so that it will download MS Windows hotfixes in the background (over a proxy) you need to specify the proxy in the underlying system. This could be done via netsh winhttp:

1.) Run a CMD as Administrator

2.) To Displays the current WinHTTP proxy setting use:

netsh winhttp show proxy

3.) To set the proxy use:

netsh winhttp set proxy proxy-server="http=myproxy;https=sproxy:88" bypass-list="*.contoso.com"

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