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Weird Email Receiving Issues with Exchange 2003

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  • Weird Email Receiving Issues with Exchange 2003


    Been working with an SBS2003 running Exchange and ran into a weird issue. Some of the users (like two out of the five users) are complaining that four or five emails a week are not being received by the recipient. They send a couple hundred emails a week between the two users. None of the other 3 users complain of this issue, but it could be happening to them too, and just not realize it. I've asked everyone to keep an eye out for any abnormal behavior coming from the network/email.

    They also complain that some emails that are sent to them are also not being received on our end. The external email addresses that they are having issues with are hosted with a number of different services. Some are Hotmail, others Yahoo, and even some and Earthlink addresses. That makes me think that it isn't a blacklisting issue considering that it is so random and not isolated to one email service provider.

    I am using the ISP's DNS servers (Comcast Seattle Area and and wondering if this could be an issue? Even though I have always had pretty good luck with these for just about everything else. I was thinking about changing them to GoogleDNS or something just to rule it out.

    Does anyone know of any reasons that this may be happening? There are some errors in the event viewer about ActiveSync and some other stuff, but nothing popping any red flags.

    Appreciate your help!


    (PS. This unit is also running as the company's DC, DHCP, DNS, File Server, IIS for Website, and I think that's about it.)

  • #2
    Re: Weird Email Receiving Issues with Exchange 2003

    Turn on logging in Exchange -- once it leaves your organisation, you can do absolutely nothing.
    Are the users getting NDRs?
    Are you using a smarthost for outgoing emails?
    How are you collecting inbound emails -- POP or SMTP?
    Tom Jones
    MCT, MCSE (2000:Security & 2003), MCSA:Security & Messaging, MCDBA, MCDST, MCITP(EA, EMA, SA, EDA, ES, CS), MCTS, MCP, Sec+
    IT Trainer / Consultant
    Ossian Ltd

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


    • #3
      Re: Weird Email Receiving Issues with Exchange 2003

      SMTP, no ndrs, and no smarthost.

      I think it is a PTR issue. I went into exchange system manager and DNS and reconfigured the PTR settings to instead of the xxx.xxxxx.local.

      Do I need to do anything with the ISP to get the PTR resolving properly?


      • #4
        Re: Weird Email Receiving Issues with Exchange 2003


        After doing some tests, I realized that the issue was with the ISP having an invalid PTR record. It was being forwarded to an email filtering service that the organization no longer was utilizing. Had the ISP switch the PTR to the public IP of the mail server and we were no longer being blocked by other email servers.

        If you are running into this issue yourself, PM me and I will help you out with fixing it.

        Thanks, and happy New Year!