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  • Outlook 2003 Connects, Outlook 2007 Won't

    I have a Windows 2008 server running Exchange 2007. I've gotten OWA to work with a self-signed cert, but new installs of Outlook 2007 on the internal network won't connect to the server. If I put Outlook 2003 on, it will connect fine, then I upgrade to Outlook 2007 and all is well. Obviously, I don't want to do that if I don't have to.

    The self-signed cert is for http://home.domain.com. Do I need to create a cert for http://server for internal clients?

    If I were to buy a cert, would I need a separate internal and external cert?

    Alternatively, is there a way I can disable whatever security stuff is causing the problem internally? I'm not worried at all about my network getting hacked internally...
    Last edited by Jocko; 5th May 2009, 16:53.

  • #2
    Re: Outlook 2003 Connects, Outlook 2007 Won't

    Buy a SAN (subject alternative name) certificate from e.g. GoDaddy (price will be < $150) and it will make your life much, MUCH easier
    Google the procedure and find the link to Sembee's site (or maybe he will be kind enough to post it)

    If you stick with self signed, you will be spending far more in support time than the cost of the Cert
    Tom Jones
    MCT, MCSE (2000:Security & 2003), MCSA:Security & Messaging, MCDBA, MCDST, MCITP(EA, EMA, SA, EDA, ES, CS), MCTS, MCP, Sec+
    PhD, MSc, FIAP, MIITT
    IT Trainer / Consultant
    Ossian Ltd
    Scotland

    ** Remember to give credit where credit is due and leave reputation points where appropriate **

    Comment


    • #3
      Re: Outlook 2003 Connects, Outlook 2007 Won't

      (sigh) Spending money wasn't really what I wanted to hear. I don't know why MS made this so hard... I wouldn't be so aggravated except for the fact that Outlook 2003 can connect. It irritates me to no end that an old product can just work.

      Is there any way I can verify that a SAN will solve the problem before I shell out money?

      And thank you for the response.

      Comment


      • #4
        Re: Outlook 2003 Connects, Outlook 2007 Won't

        Well, I've set up Exchange 2007 on Server 2008 with a GoDaddy SAN certificate in two separate environments, and each has taken me about 2 hours work to fully configure.

        Others will probably tell you the same, or you could use to find out more e.g.
        http://www.google.co.uk/search?hl=en...re+setup&meta=
        Tom Jones
        MCT, MCSE (2000:Security & 2003), MCSA:Security & Messaging, MCDBA, MCDST, MCITP(EA, EMA, SA, EDA, ES, CS), MCTS, MCP, Sec+
        PhD, MSc, FIAP, MIITT
        IT Trainer / Consultant
        Ossian Ltd
        Scotland

        ** Remember to give credit where credit is due and leave reputation points where appropriate **

        Comment


        • #5
          Re: Outlook 2003 Connects, Outlook 2007 Won't

          My Google-fu failed me because I wasn't searching for Outlook Anywhere; since that was working properly, I didn't look for anything on it. It still boggles my mind that Outlook 2003 can connect and Outlook 2007 can't when they're both on a local network... but the following links seem to provide the proper guidance.

          http://blog.sembee.co.uk/archive/2008/05/30/78.aspx

          http://blog.sembee.co.uk/archive/2008/10/16/87.aspx

          http://www.amset.info/exchange/singlenamessl.asp


          I guess I'll shell out the $60 bucks from https://domainsforexchange.net/ and see if that solves it.

          And one last time - there is no good reason why Outlook 2007 can't drop down to 2003 functionality and work. I mean, it's far more likely that some idiot user will lose his or her laptop than for some hax0r to fake a bunch of certificates and sniff my mail.

          Thanks for the help!

          Comment


          • #6
            Re: Outlook 2003 Connects, Outlook 2007 Won't

            The links are already posted to my blog.

            However be aware that Outlook Anywhere on Outlook 2007/Exchange 2007 is NOT supported with the home grown certificates. Only the commercial certificate is supported.

            Given the headaches involved with getting self signed certificates to work, it just doesn't make any sense to try and get it to work with them. Plus once you have deployed self signed certs, when you need to update them, every machine has to be touched.

            Simon.
            --
            Simon Butler
            Exchange MVP

            Blog: http://blog.sembee.co.uk/
            More Exchange Content: http://exchange.sembee.info/
            Exchange Resources List: http://exbpa.com/
            In the UK? Hire me: http://www.sembee.co.uk/

            Sembee is a registered trademark, used here with permission.

            Comment


            • #7
              Re: Outlook 2003 Connects, Outlook 2007 Won't

              Simon, following up on your assertion, just wondering if you could explain why Outlook Anywhere using Outlook 2007 works perfectly with a self-signed certificate created during the configuration process of SBS 2008. No hiccups whatsoever.

              Regards,
              Pete

              Comment


              • #8
                Re: Outlook 2003 Connects, Outlook 2007 Won't

                This is Microsoft's official stance on the use of the self signed certificate: http://technet.microsoft.com/en-us/l...EXCHG.80).aspx

                One of the key lines is this:

                "Important: The self-signed certificate is not supported for use with Outlook Anywhere or Exchange ActiveSync. "

                While you can make it work, it isn't supported.
                Personally I don't bother even trying to make it work. The headaches aren't worth it.

                Simon.
                --
                Simon Butler
                Exchange MVP

                Blog: http://blog.sembee.co.uk/
                More Exchange Content: http://exchange.sembee.info/
                Exchange Resources List: http://exbpa.com/
                In the UK? Hire me: http://www.sembee.co.uk/

                Sembee is a registered trademark, used here with permission.

                Comment


                • #9
                  Re: Outlook 2003 Connects, Outlook 2007 Won't

                  Thanks, Simon. Very clear cut language from Microsoft there.

                  The SBS team worked its magic and made the process almost foolproof, so there must have been plenty of scope to get it to work. They increased the certificate expiration date to 5 years and created an install package for remote clients to overcome the Outlook Anywhere issue. I haven't looked up what that install package does exactly, because manually saving the certificate into the Trusted Root folder is not enough to make Outlook 2007 work.

                  Regards,
                  Pete

                  Comment


                  • #10
                    Re: Outlook 2003 Connects, Outlook 2007 Won't

                    The SBS team know that most of the SBS users are tightwads and will just call support to get their "free" certificate to work. This is nothing new, with something different being doing for SBS.

                    If you want to do everything with Exchange 2007 then you need to have commercial certificate. Anything else will just give headaches.

                    Simon.
                    --
                    Simon Butler
                    Exchange MVP

                    Blog: http://blog.sembee.co.uk/
                    More Exchange Content: http://exchange.sembee.info/
                    Exchange Resources List: http://exbpa.com/
                    In the UK? Hire me: http://www.sembee.co.uk/

                    Sembee is a registered trademark, used here with permission.

                    Comment

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