From: "Scott MacLean" <[EMAIL PROTECTED]>

> Outgoing mail:
>
> IMail --> Internet
>
> User sending mail:
>
> Client --> ASSP --> IMail --> Internet

This is not related to your problem, but your outgoing configuration it is 
not correct if you have any Imail webmail users.

None of the outgoing webmail is being seen by ASSP and the recipient's 
addresses are not getting auto-whitelisted.  Imail should be configured to 
use ASSP as a gateway in the SMTP service gateway options.  The problem with 
this, I believe, is you then need a delivery service for ASSP.  I use IIS 
SMTP for outbound SMTP only and it listens on a port that is firewalled from 
the internet.

So, client --> mailserver port 587 --> ASSP second listen port --> Imail 
incoming port --> ASSP Relay port --> MS SMTP --> Internet

Additionally, I have installed hMailserver and clamAV for win32 to act as an 
SMTP AnitVirus/AntiPhishing gateway between ASSP and Imail.  No domains are 
set up in hMailserver, just a route for SMTP to my domain mailserver port.

So my setup is:

Incoming from internet -->(port25) ASSP
ASSP SMTP destination -->(port125) hMailserver with ClamAV
hMailServer target SMTP route -->(port225) Imail SMTP --> Client

Outgoing from client webmail -->Imail webmail
Imail Remote getway host -->(port325) ASSP relay port
ASSP Relay Host -->(port425) MS SMTP --> Internet delivery

Outgoing from external client SMTP -->(port587) ASSP second listen port
ASSP SMTP Auth Destination -->(port225) Imail SMTP (if you have Imail 8.22 
or 2006 you can set up Imail's ability to listen on port 587 for incoming 
auth connections I think, so ASSP's auth destination would be that)
Imail Remote getway host -->(port325) ASSP relay port
ASSP Relay Host -->(port425) MS SMTP --> Internet delivery

I think i got that right. :o)
The downside to using a gateway in front of Imail is your users will have to 
reconfigure their clients to connect to port 587 (or any you choose) for 
outgoing smtp.  The gateway doesn't know about your clients so they have to 
talk to your MTA, Imail directly.

Good luck,

Doug Traylor 



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