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  • TLS instead of SMTP

    What if I sent all my outgoing email via TLS using Exchange 2003?

    I believe the way Exchange 2003 SMTP conncetors work are as follows:

    TLS to TLS
    1. My connector tries to TLS to Tyler's TLS connector
    2. Tyler's connector has the StartTLS verb so Tyler's connector accepts my conncetion and email flows.

    TLS to SMTP
    1. My connector tries to TLS to Marla's SMTP connector
    2. Marla's connector does not have the StartTLS verb so Marla's connector terminates my conncetion.
    3. My connector reverts to SMTP, retries the the same email and email flows.

    Is this correct?

    Also, for TLS to SMTP, I'm guessing that for the most part, steps 2 and 3 take a negligible amount of time. Is that correct?

    Thanks

  • #2
    Re: TLS instead of SMTP

    http://support.microsoft.com/kb/829721

    Considering most MTA's arent using the TLS standard it kind of defeats the object of having a secure SMTP conversation when it reverts back to SMTP. Also all your mail clients would need to be configured to use TLS/SSL.

    Comment


    • #3
      Re: TLS instead of SMTP

      TLS on Exchange 2003 is either on or off, and the remote site needs to support it. Exchange 2003 cannot do opportunist TLS, so if you enable TLS you will find that you are unable to send or receive email to the vast majority of email hosts.

      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


      • #4
        Re: TLS instead of SMTP

        I mixed Exchange up with what Postini can do. I configured my exchange environment to send and recieve email to and from Postini via TLS. Postini is an anti-spam/anti-virus hosted solution owned by . I configured Postini to send outbound from us in TLS and downgrade to SMTP if the recipient does not have the STARTTLS verb when you Telnet. This causes a tiny delay in mail flow but works like a charm. I had hoped that Exchange had this kind of set up natively but I guess not.

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        • #5
          Re: TLS instead of SMTP

          Exchange 2003 cannot do that. Exchange 2007 can.

          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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