>The client being the end user or the Mail Server? 

the client

>I'm currently using pfSense 2.1.5

IMHO one of the best you can have. So you may trace using the buildin 
pfSense trace (packet capture) function.

Thomas





Von:    Doug Lytle <[email protected]>
An:     ASSP development mailing list <[email protected]>
Datum:  01.12.2014 15:46
Betreff:        Re: [Assp-test] Remote SMTP issues with TLS



>> Maybe I need to read up on tcpdump.

>> trace the connection between the client and assp.

The client being the end user or the Mail Server? 

If the end user, this is happening on all of them, including my test 
laptop on a MiFi wireless service.  If that's the case, maybe it's my 
firewall.  I'm currently using pfSense 2.1.5

Doug

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