Hi Mark,
Have you tried the following test: while Lookout being on domain1, you use domain1's mail server to email a domain2 user? I am pretty sure that would work. This is because SMTP assumes the mail is being sent from within the domain (in our test, Lookout was on domain1 and you used domain1's mail server).
I am guessing you tried using "external" SMTP servers (i.e., those different from what Lookout is on). To send mail using an "external" mail server (for instance that of an ISP) is tricky. I know of two options; there are more:
(1) ESMTP, and
(2) POP-before-SMTP.
ESMTP: 'Enhanced (extended?) SMTP' has authentication and accepts username and password. Not all mail servers suport ESMTP, however. In any case there's no option in Lookout's Mailer object to send username and password, so that's ruled out.
POP-before-SMTP: Looks like most ISPs use this mechanism. The idea is that the user first "POPs" the mail server, i.e., connects via POP (and retrieves?) the mail. When this happens the IP address of the user is logged (this mechanism is called POPAUTH). From then on and for the next 15 minutes (default), the user from that IP address can send mail using the SMTP. This is mainly to prevent unauthorized "relaying" of mail by spammers and others. And that's the "Unable to relay" error you're getting.
By the way, emailing users local to the SMTP server is not considered "relaying," which is why you observed "...as long as i use the same SMTP server that the recipient is using, the e-mail will go through..."
So, what is the solution? I guess the easiest would be to use the mail server from the domain on which Lookout resides. If you have to use another SMTP server, you may want to "POP" the server first by reading email off of it somehow -- this doesn't seem very practical. Maybe you could talk to the ISP / Mail server administrator to make an exception for mail coming from the Lookout machine (IP address); again not sure if this is doable.
Well, I hope this helps in at least understanding the problem... if not in solving it

Regards,
-Khalid
Message Edited by Khalid on 12-03-2005 12:20 AM