It's either my mail server or the firewall in terms of a setting i have wrong or i missed. When the mailserver tries to send mail from it goes to the right external ip but the packets die. I have setup a packet filter rule to allow that traffic to no avail. I have port 25 form the outside forwarded to the box in question(it runs zimbra). When i try to telnet to port 25 it hooks in. When i try to telnet to port 25 it times out. I've also setup hosts definition of to to no avail on the mail server. I can ping it form the mail server but port 25 traffic won't make it. Maybe it won't due to the fact it's a loop. I may have to mod the mail server internally so root@ heads to it's internal address. FYI originating ip for the mail in question is the loopback address I know it's got to be something simple..any ideas?