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Distribution list with external email contact does not send the mail externally

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  • Distribution list with external email contact does not send the mail externally

    HI
    I have a SBS 2008. We have an AD with 30 users and 2 external mailcontacts belonging to a subsidary of us having their mail at a local provider.

    I have a distri list called: [email protected]
    In that list I have 5 internal contacts and 2 external contacts
    [email protected] and [email protected]

    When I send a mail from my home account to [email protected] everyone receives the mail except the 2 external ones.

    When I send a mail from inside the company it works.

    When doing a research in the EMC tool (Message Tracking) I have following sequence:
    EXPAND - ok
    TRANSFER - ok
    FAIL SMTP

    unfortunately I can not go further, clicking next on FAIL SMTP does not give any details. it says server "isp relay server" not found.

    Anyone an idea?

  • #2
    Re: Distribution list with external email contact does not send the mail externally

    can your mail users normally send email out of the domain ?
    What happens if you try and send an email direct to [email protected] from [email protected] ?
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    • #3
      Re: Distribution list with external email contact does not send the mail externally

      Yes,

      The environment exists since 2010 and we have no issues whatever with emails in or out the company. OWA is working fine, outlook also. Only what I mention is not working as it should.
      Mailing the external contact is working fine if you use it from within the domain/company. Mailing from external is working but not for external contacts in the distri list
      Thank you for any help or idea you might give

      Erwin

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      • #4
        Re: Distribution list with external email contact does not send the mail externally

        did this distribution list with the external contacts ever work ?
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        • #5
          Re: Distribution list with external email contact does not send the mail externally

          I am pretty sure that the remote server is rejecting the email.
          Most likely because the email is coming from a domain it doesn't recognise as being able to send from your IP address. It is seeing the From address of the original sender and believes your server is spoofing it.

          Not really a lot you can do about it. Rewrite the headers so that the email comes from the group (which is how commercial email list software works) would be about the only option, but then replying to the email will be difficult.

          Simon.
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          Simon Butler
          Exchange MVP

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