if you have 2 Imail server handy (my 2nd Imail server happens to be my own w2k workstation for remote admin purpose that has never worked, but I am using it for testing purposes only), maybe you can try switching the SMTP port on both Imail servers to something else (after business hours for a few minutes only) and you can probably see the result yourself in the log file.
(I also have a 2nd personality setup in my Eudora Pro for test purposes, having the smtp and pop3 servers configured to the name of my own pc)
Webshield can be configured several ways to handle different SMTP traffic scenarios, see this link: http://pumi.org/geza/temp/webshield.jpg
Geza
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