Let me jump in with a question...
If you are using POP3 to talk with the server, the issue might be the order of mail retrival.. alot of ISP mail providers now require you to SEND mail by first RECEIVING mail then sending it. THis is to aid in cutting down spammers who are trying to relay the mail through their servers.
If you have your own server, then this probably doesnt apply at all.
But, with a sniffer on your end, you can verify the mail exchange.. move the sniffer to the remote end and verify it again. Divide and conquer the problem.
More thoughts.. if you get mail, then the server can see you.. if you do not have a route back to the server, you more then likely could not send the mail. I read somewhere in the thread you could not ping the mail server. thats a problem if it's still an issue. Run a traceroute from the workstation adn from the router. On the router, use a extended traceroute, force the router to use the port connected to the wan link. See where the packets are being droppped.
Are you configured for network browsing? If so, then try mapping the server via the "whack-whack servername" and see if the mail works that way.. if so then the issue is a name resolution problem.. WINS more then likely and/or DNS
MikeS
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"Diplomacy; the art of saying 'nice doggie' till you can find a rock" Wynn Catlin