Yes, we use Mailsweeper to send mail out. The IMC has a forced route to the IP address of the Mailsweeper server and not hostname. The Mailsweeper then sends it on. Yes we have firewall between the DMZ and the Exchange Bridgehead. But Iam told all the rules are setup correctly on the firewall. I can telnet to the mailsweeper server from the bridgehead fine (port 25). even when I retry the delievery of the pending message it still fails. I have done maximum loging on the IMS connector and no information about that message is found.