>As it turns out, MS supplies the "Outgoing Domain" name in the HELO >command. I'm testing a version now that supplied the primary IP address >of the Mac instead.
I have tried using the Macintosh Version of MS Express which is what I think you were talking about this presents the IP address of the sending machine after the HELO in square brackets.
This appears to basically suffer from the same problem so changing TF MS to work this way will not work in 100% of cases.
So it appears that unless the server is presented with the host name it makes no attempt to verify that the IP address is correct, it only verifys that a host name resolves to an IP does this make any sense.