This leaves me with a problem, if I set Webshield to listen on port 25 and pass on mail that's found to be clean then the DNS Blackhole feature of IMail will become disabled because all mail will be seen to be coming from the internal servers IP address (Webshield SMTP adds its own Received header).
Correct. That's how most anti-spam products work (ours was actually the first to scan multi-hops, allowing scenarios such as yours to work).
Is there a way to have IMail ignore received headers from the localhost address and look back at the previous received header to see where it came from before it hit the localhost?
IMail v8's anti-spam cannot do that; you would need an addon (such as our Declude JunkMail) to do that.
Or can you think of any other configuration that would allow WebShield SMTP to interact with the IMail server so that IMail answers the door (so to speak) on port 25 passes the SMTP traffic off to WebShield which then passes it back to the IMail message store on another port?
Unfortunately, you're stuck -- you want WebShield to run before IMail, which means that IMail won't see the IP of the remote mailserver (you have a choice of it seeing 127.0.0.1 if WebShield runs on the same server, or the internal IP if it runs on another server).
Since you already have anti-spam software in your setup, you may want to use it instead of the IMail v8 anti-spam.
-Scott
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