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Mail & Groups in Exchange?

I've added this as part of another thread but don't want to lose track of it so here goes:

I have a distribution group in Exchange eg distgroup@mydomain.com

In that distribution group is 2 contacts external to the domain eg me@gmail.com & me@hotmail.com

Mail leaves Exchange and is filtered via the UTM

Now the strange part:

1. If I use an internal user eg somebody@mydomain.com to send the distribution group, exchange forwards it to the UTM which in turn forwards it to both email addresses ie me@gmail.com & me@hotmail.com. The UTM logs it etc and everything works well as it should.

2. If I use an external email address, specifically me@gmail.com and send to dist@mydomain.com, exchange does it's part  and sends it to the UTM and the UTM logs email as being sent out (both to me@gmail.com & me@hotmail.com). The mail reaches me@homail.com but not me@gmail.com (the original sending address to the distribution list)

3. If I do the same as above but use me@hotmail.com as the original senders address to the distribution list, mail arrives at me@gmail.com but doesn't at me@hotmail.com (UTM records it as received at both gmail & hotmail servers)

Any ideas?



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  • Show us the log lines related to 2 or 3.

    Cheers - Bob

     
    Sophos UTM Community Moderator
    Sophos Certified Architect - UTM
    Sophos Certified Engineer - XG
    Gold Solution Partner since 2005
    MediaSoft, Inc. USA
  • Hi Bob,

    there's nothing untoward in them. The UTM sends the mail and it is accepted. So it's doing it's job. Somehow, the email service (both hotmail & gmail) doesn't want to show the email. Searched all over for it in both accounts and can't see it. Really strange.