Port 443 in proxy actually blocking sites

Discussion in 'Mac OS X Server, Xserve, and Networking' started by gopherhockey, Mar 22, 2011.

  1. gopherhockey macrumors regular


    Apr 2, 2010
    Our company uses Microsoft ISA servers to proxy externally. As such, we have to set the proxy settings on the Mac to proxy.company.com and port 80, 443 respectively.

    The trouble is, 443 as an SSL port does not work. If I set the HTTPS proxy port to 80, it works.

    What then breaks is autodiscover, which is used to direct Outlook 2011 to the correct Exchange 2007 web access server.

    So right now we can set the HTTPS port to 443 and Outlook will work but secure web sites do not, or we can set it to 80 and Outlook does not work.

    We do have internal web site domains set to bypass the proxy.

    I have our proxy guys coming up to look today but wondered if anyone has seen anything like this. These are the same settings our Windows users have, and it works just fine for them.
  2. assembled macrumors regular

    Jan 12, 2009
    hmm, I would guess that they have a different auth requirement for HTTPS....
  3. R3Z4N macrumors newbie

    Mar 31, 2011

    I am having the exact same issue. Did you manage to resolve this? The proxy at work is the same for Secure Web (HTTPS) and Normal (HTTP).

    How do I resolve this?


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