Question : Delivery Receipt's getting Queued

We're running Exchange 2003 SP2 on three servers in the same site, one of which is a Frontend server, set up to act as a smarthost for the other two, which house the mailboxes.

Everything works great except that, when users request Delivery Receipts from the outside, the receipt ends up in the  "messages queued for deferred delivery" queue on one of the mailbox servers. When I look a the email in the queue, it shows "Envelope Recipients: SMTP:[email protected]m;". My users do not have SMTP addresses with that domain name, but when I added one to my account and tested, received a receipt message. I realize that adding SMTP addresses like that through a recipient policy is an easy work around, but I'd rather keep it simple and figure out what I'm doing wrong.

It seems like this problem has something to do with the FQDN and Masquerade domain info set in the Advanced Delivery section of the Default SMTP Virtual Servers on the backend.

Any ideas?

Answer : Delivery Receipt's getting Queued

The way that you are doing it at the moment is NOT correct. Therefore I suspect something else is wrong with the transport flow.
Smart host is basically a very blunt object way of sending the email between the servers - it is forcing it through. Exchange should route the email correctly on its own. Therefore something is wrong.

Removing the FQDN will cause problems, so you should put it back in. However it should be unique on each server and resolve correctly inside.
On the SMTP virtual server, ensure that it is set to a specific IP address, rather the "All Unassigned". If you then have routing group or SMTP connectors, recreate both.

SMTP connectors should be used to route email out of the Exchange org. Smart host on the SMTP virtual server should not be used under any circumstances - that is just a setting left over from the IIS SMTP and simply causes problems.

Simon.