> -----Original Message-----
> From: Steve Moffat [mailto:Steve@...]
> Sent: Monday, April 25, 2011 8:13 AM
> To: 'assp-test@...'
> Subject: [Assp-test] Outgoing mail not going through ASSP
> I have a set up as follows. ASSP version 2.0.2(3.0.13) and Mailenable
> same server. Win2k8R2.
> I have had to use separate IP's for ASSP, (192.168.100.25), and
> (192.168.100.26), in order to have TLS operate. If I put them on the
> with different ports, there is no STARTTLS offered therefore TLS
> Can anyone help me out with this? As the emails are not being picked
> ASSP then auto whitelisting is not working.
Is outbound traffic on your mail server going through your ASSP Relay
Port? If you want whitelisting (at least in ASSP 1.x), the outbound
mail has to be going through that port. I'm assuming it's the same in
So, for example, ASSP listens on 192.168.100.25 for all incoming SMTP
sessions. It should also listen for Relay connections. So, you could
configure it to listen on 192.168.100.25:125. Now setup your mail
server to send outbound mail to 192.168.100.25:125. You will also need
a relay host configured. So, you can setup another SMTP server
(assuming you can have more than one, I can with Exchange) on your
Mailenable that is only used for outbound to the Internet. Configure the
IP of your other SMTP server with something like 192.168.100.27 and then
configure ASSP with that address in the relay host. I don't know if
this will work in your environment, but theoretically it should.