>> Do you have multiple IPs? If you set listenport to 25 nothing will  
>> pass ASSP regardless of IP.

> Yes, I have multiple IPs on the box, but only one IP is noted in 
> their collective DNS records as being the MX server for all 
> those domains/IPs.

that's ininfluent; as long as port 25 is published on an IP a simple
portscan would reveal it; don't think it's done by humans there are
bots out there just doing that over and over, and once they find an
SMTP server ...

>> I'm almost 100% sure (I never say 100%) that 2 apps can't run on 
>> the same ip:port simultaneously....

> So am I. 

for sure; but... let's say you have two IPs; you set ASSP to listen
on 1.2.3.4:25 and point the MX to that IP; next you set the SMTP
server to listen on 1.2.3.5:25 at that point, assuming bot IPs are
public and assuming the second one is unfiltered, anyone will
be able to connect to 1.2.3.5:25 and bypass ASSP; but I don't
think this is the case (or better said not exactly) since you see
email coming from 127.0.0.1 so there must be "something else"
accepting such messages and then "proxying" them to the
SMTP listening on 127.0.0.1 ... hmmm... the AV scanner maybe ?

> Also, assp demonstrates this when it closes improperly: when 
> restarting, sometimes it complains that the port is in use by 
> another application (its older self). Restarting the box always 
> gets things back to normal.

ARGH... so there's something else listening on 25 and on the
public IP :P bad config man, really bad; I suggest you to stop
ASSP and then check the listening ports on the box and find
out what else is trying to listen on port 25... and fixing the setup
for this latter application


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