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Exchange 2010 : Getting headaches with Certificates !

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  • Exchange 2010 : Getting headaches with Certificates !

    Hi Everyone,

    I really need your help after spending a hell lot of time looking for a guide. I am not bad in Windows Server installations / configurations, as well as Exchange Server, but there's one thing I hate: Certificates! I just cannot understand anything!

    Well here is my situation:

    I have the following infrastructure:

    · - One Windows 2008 R2 acting as Domain Controller (2008 R2 Functional Level)
    · - One Windows 2008 R2 with Exchange Server 2010 SP1 with the standard configuration (All roles except Unified Com)
    · - Internal Domain Name: mega.local (Fake one, of course
    · - External Mail Server: mail.megamail-ltd.com (Fake, as above
    · - PopCon fetches mail from my external server and delivers them to local mailboxes.
    · - We have dynamic IP Address with ADSL, I therefore created a dyndns account and an updater on my exchange, the address being : mega.dyndns.org

    As stated above, all setup configurations are left default… I therefore did not touch anything related to certificates.

    OWA is working perfectly fine, except that it says that the certificate is not trusted (Internally (megamail.mega.local/owa) and Externally (https://mega.dyndns.org/owa)), but it works! (I have forwarded OWA port in my simple ADSL Router to my Exchange Server)…

    However, I need to make Out Of Office to work, and Outlook Anywhere… this is where I am getting deep headaches ! Basically, I don’t know how to buy a certificate, how to generate a request, which name to put, etc, etc and etc…

    Can someone help me on this? I have googled and googled a lot but did not manage to find a proper step by step guide…

    Thanks a lot in advance for your precious help.

    Cheers

    Laurent

  • #2
    Re: Exchange 2010 : Getting headaches with Certificates !

    Dead easy -- lots of advice:
    http://www.google.co.uk/#sclient=psy....,cf.osb&cad=b
    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 **

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    • #3
      Re: Exchange 2010 : Getting headaches with Certificates !

      If you are using a dyndns host name then it is unlikely that you will be able to buy an SSL certificate for that domain because it isn't yours.
      What you will need to do is use your email domain, possibly using CNAMES to map the required DNS entries to the dynamic DNS host name. I guess if you are using dynamic DNS it is a lab or home environment.

      I have instructions on the process here:
      http://exchange.sembee.info/2010/ins...sl-request.asp
      Although I don't go in to the purchase and request of the certificate with the vendor, because they are all different and will have instructions on their web site.

      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.

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      • #4
        Re: Exchange 2010 : Getting headaches with Certificates !

        Ok thanks. Is there a website where we can have free SSL cert for test purposes, or 30 days trial for ex?

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        • #5
          Re: Exchange 2010 : Getting headaches with Certificates !

          One or two...
          http://www.google.co.uk/#sclient=psy....,cf.osb&cad=b

          Thank you,
          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

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