WSUS 3.0 SP1 introduces a new command line tool to help admins set different upstream proxies (one for HTTP and one for SSL). You could set the same proxy server, but running different proxies for HTTP and SSL on different ports.
Currently there is a problem with either one of the following components:
In either case, the result is the same: WSUS will always only use the proxy specified for HTTP.
The work-around is to add the extra value to the SUSDB database. WSUS looks to this value, and if configured, will use the separate SSL proxy.
So here’s the procedure:
UPDATE dbo.tbConfigurationA SET UpstreamServerUseSSL = 1
Remember that Product Support doesn’t like WSUS databases which have been “tweaked” with external commands, so use this sparingly.
There is a fix on the way, but until then I hope this helps anyone else out there who stumbles on this problem.
WSUS 3.0 SP2 has fixed this. You can get this here.