Looks like there is a bug in the way automatic detection of proxy servers works with Internet Explorer. I've confirmed it on Windows 2003 SP1.
If you have enabled the option in IE to check for revoked server certificates, SSL sites fail. If you manually specify the proxy server, SSL sites work.
It appears the mechanism used for checking if the certificate is revoked can't automatically detect a proxy server. If you turn that option off (which is recommended for performance reasons) then you can live with automatic detection.
Here is some more info on IE proxy auto detect.
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