I had the SMTP service set up to relay for the loopback address. I wasn't using any objects or scripting languages to test with, I was just telnetting into the service (telnet localhost 25) and typing in the commands manually. There error I kept getting was "Unable to deliver the message because the destination address was misconfigured as a mail loop." So far I've had no luck deciphering what this error message actually means. :-/ I've since changed the configuration so that the server monitors only 1 IP address, and does not respond on the loopback. I'm technically running 3 SMTP services on this system. I have an SMTP proxy running on my main e-mail IP address, on port 25. I have my main mail server running on the same IP address, on a different port. All mail to this server comes through the proxy (AV checks, DNSBL, Bayesian filtering, etc.) The MSSMTP service watches a different IP address, and is not used in conjunction with any POP3 or other service. I have a custom program that picks up the incoming messages from the Drop folder and processes them. I'm using this SMTP service sort of as a message queuing system for distributed communications. The problem is, I have to be able to send messages back to the other application via SMTP. I can't set the proxy to relay, because it's not a real SMTP service, it just relays to the other mail server. The other mail server won't allow me to "watch" port 25 on the loopback and the other port on it's primary IP address. It watches the same port on all watched addresses. I'm just trying to avoid having to install a 4th SMTP-related service on the machine. I have access to a relay server, but I'm trying to avoid using it, as I want to have control over the retry intervals if initial delivery fails.
Grim
(aka Toby)
MCDBA, MCSD, MCP+SB
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