I sent this question into a friend at Microsoft because it has me completely stumped.  I thought I'd post it here as well to see if anyone else might have an idea.
 
I have a problem that should theoretically have been a simple resolution, but for the life of me I have not been able to figure it out.  I have a server that is used to host the Intranet for the company, which also serves as a closed relay to relay mail from an internal application to the Exchange server.  It is a Windows 2003 server w/ IIS 6.
 
A few months back I configured everything and it has been running fine ever since, as of yesterday afternoon it suddenly stopped working with no explanation.  There are no errors logged, the mail is not backing up in the Exchange queue, the mail just seems to disappear once it is sent from the relay.  I have tried enabling diagnostic logging on the Exchange server, but that was a no go.  It doesn't even appear as though the mail is routed to the Exchange server at all.
 
I have tried manually relaying a message by telnetting to SMTP on the server (as well as others which I have configured for testing) and all of which are unable to relay.  I have also tried changing the authentication methods, and using a different user account (including my own). 
 
The bugger is, I can relay directly through the mail server itself without any problems but I can't relay to it.
 
I'm about ready to pull out my hair on this one.
 
Thanks in advance!

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