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Unable to send emails through telnet using Exchange 5.5

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  • Unable to send emails through telnet using Exchange 5.5

    Hi Guys,

    I'm pretty stumped on this one and wondered if anyone had any ideas:
    Basically one of our support clients is running Exchange 5.5 (I know I know) and they can send and recieve external emails fine from Outlook. However, they need to use a program that sends automated emails through their exchange server to external recipients and this doesnt seem to work (and has never worked).
    So the first thing I tried when I heard about this problem was to just telnet in to the exchange server on port 25 and send an email through that. All looked fine, the SMTP service returned the normal 250 OK message... but then the email never arrived at the external recipient's inbox.
    All of the emails get forwarded from the exchange server to an external spam filtering company and I've contacted them and apparently the test emails are not hitting their server so its not even leaving the exchange server.
    I checked the admin mailbox and found the following NDR relating to the test emails I had sent through telnet:

    The following recipients did not receive the attached mail. Reasons are listed with each recipient:
    <[email protected]> [email protected]
    MSEXCH:IMS:XXXXX:XXXXX:EXCHANGE 0 (000C05A6) Unknown Recipient

    (those XXXX bits are just where I have replaced the domain name and exchange org name etc)


    So basically it looks like exchange thinks it is responsible for delivering the outbound messages to internal recipients... but I cant understand why this only happens with telnet mails and not normal emails sent through Outlook. I also have no idea how to tell it to think otherwise!

    I noticed that there is no SMTP service running on the exchange box, but apparently this is normal because Exchange 5.5 uses the Internet Mail Service instead... and something must be waiting to send messages via SMTP as I get the normal MS ESMTP banner when connecting to port 25 via telnet.

    Anyone got any ideas?

    Thanks
    Chris
    Software for IT Pros that I've written: http://www.cjwdev.co.uk/Software.html

    My blog: http://cjwdev.wordpress.com

  • #2
    Re: Unable to send emails through telnet using Exchange 5.5

    Oh and also, I just tried placing a test EML file in the Pickup directory under the Exchange IMS folder and this sent fine. So its definitley just when sending through SMTP via telnet etc that this problem occurrs...
    Software for IT Pros that I've written: http://www.cjwdev.co.uk/Software.html

    My blog: http://cjwdev.wordpress.com

    Comment


    • #3
      Re: Unable to send emails through telnet using Exchange 5.5

      If the application is sending email out to external recipients then I would set it to use the ISPs SMTP Server instead of trying to bounce them off Exchange. More efficient and means you don't have to configure relaying on the Exchange 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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