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SBS 2003 - SMTP Outbound Problem

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  • SBS 2003 - SMTP Outbound Problem

    I have been experiencing some SMTP outbound problems lately and am stumped. A client sends an email to an outside address, exchange picks it up, sends it out, but it never arrives. Tried multiple addressess on different domains. Same problem. I have run the SBS 2003 BPA and everything is clean. Ran the Exchange 2003 BPA and it was clean.

    I am using a smart host configuration due to some previous reverse DNS lookup delivery issues on the other end of the connection and have no choice but to continue doing so. My ISP is HughesNet.

    I have seen a consistent problem in the attempted delivery portion of the exchange. The connector will have to retry several times, each time getting an AUTH error. Eventually it will succeed (apparently), but the email never reaches the destination. No failed delivery report either.

    The number of emails I send out averages a couple a week max, so no SPAMMING on this end.

    Help!
    David Casey CISSP/CISM/SnortCP | Sr. Security Analyst | SBS 2003 R2 | ISA 2006

  • #2
    Re: SBS 2003 - SMTP Outbound Problem

    If there are authentication issues then my instinct is that the issue is with the ISP. Many ISPs have clusters of servers and if one of the servers in the cluster is playing up then that can cause this type of problem.

    Do you have message tracking turned on? If so, what does that show? If that shows the message going out then the message is being lost after being delivered to your ISP.

    The only other thing it could be is the greylisting bug.
    http://theessentialexchange.com/blog...eylisting.aspx

    However it is unusual to see that with an ISPs server.

    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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    • #3
      Re: SBS 2003 - SMTP Outbound Problem

      Originally posted by Sembee View Post
      The only other thing it could be is the greylisting bug.
      http://theessentialexchange.com/blog...eylisting.aspx Simon.
      You know, that sure does sound like a possibility. Do you know anyone who has the hotfix? I don't want to pay M$ for a call and the next service pack is a long way off to wait for. I am in the Microsoft Partner Program so I might be able to get it through that, just not sure. I did apply the registry change.

      Thanks Sembee!
      Last edited by Sembee; 8th December 2007, 19:10. Reason: Fixing URL for anyone else looking at the question - it needed a space!
      David Casey CISSP/CISM/SnortCP | Sr. Security Analyst | SBS 2003 R2 | ISA 2006

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      • #4
        Re: SBS 2003 - SMTP Outbound Problem

        Distributing hotfixes is against the license agreement - anyone doing so is in legal hotwater.
        Furthermore you don't have to pay for hotfixes - you can phone up and get the hotfix for free.

        You can also ask for them online...

        https://support.microsoft.com/contac...1410&WS=hotfix

        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


        • #5
          Re: SBS 2003 - SMTP Outbound Problem

          Was not aware of that...

          I have submitted a request as a MSPP for the hotfix. Hopefully its free

          Thanks for the advice!
          David Casey CISSP/CISM/SnortCP | Sr. Security Analyst | SBS 2003 R2 | ISA 2006

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          • #6
            Re: SBS 2003 - SMTP Outbound Problem

            Just wanted to close out this thread. I applied for and received the hotfix from MS free of charge. Solved the problem. Easy!

            Thanks to all for their help!
            David Casey CISSP/CISM/SnortCP | Sr. Security Analyst | SBS 2003 R2 | ISA 2006

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            • #7
              Re: SBS 2003 - SMTP Outbound Problem

              Thanks for posting back with the update David. It is appreciated.
              1 1 was a racehorse.
              2 2 was 1 2.
              1 1 1 1 race 1 day,
              2 2 1 1 2

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