I need to be able to send messages from my exchange server to outbound servers on both port 25 and port 2525. I have the exchange server determine which port to send on via the Address Space rules in my connectors. I setup 2 virtual smtp servers, one with port 25 outbound (send direct) the other with port 2525 outbound (authenticated smart host). I would think this setup would work fine, but messages sent via the connectors to the virtual server using 2525 get bounced with an error message:
Your message did not reach some or all of the intended recipients.
Subject: test RELIABLE 2525
Sent: 5/10/2006 12:09 PM
The following recipient(s) could not be reached:
firstname.lastname@example.org on 5/10/2006 12:09 PM
A configuration error in the e-mail system caused the message to bounce between two servers or to be forwarded between two recipients. Contact your administrator.