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our company (only 4 employees) has one SBS 2008 and on it Exchange 2007. When we send mail to one contact, exchange does not deliver the mail.

When looking at Message Tracking Results I see that the mail is received from the local user with an EVENTID of RECEIVED and the correct email address is in the Recipients field, but when the same message is in the EXPAND eventid then the Recipients field is empty and the email address that is being sent to is in the RelatedRecipientAddress field, and there it stops and disappears (nothing in Queue). No SEND eventid appears for this email address.

Sending mail to other email addresses works fine, this email address that is causing problems is a gmail address but sending to other gmail addresses works fine.

I think a previous admin here tried to do some magic with this address so there might be some rule that is causing this but I don't know Exchange well enough to debug this. Any pointers towards debugging this?

TIA

  • Can you check if there are any rules against outbound mailflow? – Proxy Feb 6 '15 at 16:13
  • I could if I knew how to :-) First time administering an SBS, so I am not that familiar with rules or how to check them. – ojs Feb 6 '15 at 16:19
  • SBS2011 comes with Exchange Server 2010, not Exchange Server 2007. – joeqwerty Feb 6 '15 at 16:23
  • ah, sorry, right, this is SBS 2008 – ojs Feb 6 '15 at 16:31
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For some reason there was a Distribution Group that had this email address as it's primary SMTP address and when I disabled that group the mail flow resumed as normal.

  • Found out that the DG was created to allow forwarding an internal address to an external address (the gmail one). But that obviously did not work. So removing the DG, creating a normal Mail Contact and using that to forward to the gmail address seems to do the trick. – ojs Feb 6 '15 at 17:26

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