I've been banging my head against this all afternoon. I have a pbx on my LAN that needs to send mail. Unitl now, I have only been sending to users on my domain which has been working. Now, however, I need it to be able to send mail (failure events, for example) to outside addresses. I have my exchange (2007) configured with a nice new connector that listens on port 2525 and if I send outside mail through it via telnet (from the pbx) by using manual smtp commands, all is well. I just can't get sendmail to see it as a relay. It thinks it's relaying, but it always relays to 'localhost' which then fails because the pbx can't authenticate with the ISP. I have been through the forum atricles and I have tried all manner of specifying HOSTS and RELAYs in sendmail.mc but I must be missing something. I am make-ing a new /etc/mail and restarting sendmail each time. resolv.conf and hosts are correct - everything else is fine. Can somebody send a link to some directions for this - or help me through it? Thanks