> 1.  Does one need a smarthost for outbound mail?
> (Or can ASSP handle sending direct to destination MTA)

This depends on your configuration.  In my case yes.  I have:
User=>MTA=>ASSP=>MS SMTP=>Internet

This differs in a key way from the other accepted configuration of:
User=>ASSP=>MTA=>Internet

If your MTA has an integrated web mail feature you may have to use the first 
configuration if you want the web mail to be seen by ASSP for 
auto-whitelisting of recipients.  Since you mentioned a smarthost, it sounds 
like you might be using Exchange, and in fact your email headers seem to 
corroborate that fact, so your configuration is similar to the web mail 
config and you have to configure sending through a smarthost which goes 
through ASSP first and then an SMTP sending service of your choice, I'll use 
MS SMTP for the example:

User=>Exchange=>smarthost (ASSP relay port)=>MS SMTP=>Internet

See: http://www.asspsmtp.org/wiki/Configuration
http://www.asspsmtp.org/wiki/HOWTOS#Microsoft_Exchange_HOWTOs

And here is a Google cache write-up on using ASSP with Exchange:
http://tinyurl.com/2oe7ab
or
http://72.14.253.104/search?q=cache:TQZbdJXokKsJ:www.andersonit.com/assp/ASSP%2520Installation%2520with%2520Exchange%25202000.doc+assp+installer&hl=en&ct=clnk&cd=2&gl=us&lr=lang_en

http://www.andersonit.com/assphowtoe2k.htm

> 2.  If ASSP listens on only 1 port , how can it distinguish between
> incoming and outgoing SMTP actions?  (Or does relay have to be set)

Relay listen port is different than the Listen port.

ASSP has another listen port for outgoing connections to be sent from your 
MTA to ASSP.  Depending on who is sending through ASSP you may or may be 
connecting to it from outside of your local network.  I have one network 
that allows email to be sent from outside the network.  Those users connect 
to port 587 of my server which goes directly to my MTA'a authentication 
port.   Mail is then routed internally or externally as needed, only 
external mail goes through ASSP.  I have another site sending email from 
inside only, so they connect to their MTA's SMTP listen port which is not 
available to the internet. Then the MTA sends the email internally or 
externally, with external mail being routed through ASSP.

In both these cases, routing the external mail calls for the MTA to send to 
ASSP's relay listen port which is not available to the Internet and then 
ASSP hands that off to the SMTP delivery service which is also not available 
to the Internet.

If you don't use Auth and have external users sending through your server 
(why would you?) you could have then connect to the same SMTP port that you 
are receiving email on for your domain.  ASSP would pass it along to your 
MTA (Exchange) and then it would get routed to the intended recipient.  The 
best practice is to have authorized sending users to connect directly to 
your MTA with the email bypassing ASSP until the MTA is routing it out to 
the Internet.

Doug Traylor 


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