APC 9630 cannot send SMTP

[apcuser123456789]

apc 9630

app OS 7.0.8

app module 7.0.8

apc monitor 1.0.9

I cannot send smtp emails. I have tried all options available. 

The mail server reports this

*5309 peer closed connection in SSL handshake while SSL handshaking, client: 192.168.1.23, server: 0.0.0.0:465
*5320 client 192.168.1.23:34164 connected to 0.0.0.0:465

For example my Pfsense server can send SMTP notifications with the exact same settings.

*5576 client 192.168.1.1:2890 connected to 0.0.0.0:465
*5576 client logged in, client: 192.168.1.1, server: 0.0.0.0:465, login: "notifications@mydomain.net", upstream: 10.0.3.4:10025
*5576 proxied session done, client: 192.168.1.1, server: 0.0.0.0:465, login: "notifications@mydomain.net", upstream: 10.0.3.4:10025

Has anyone ever seen this?

Thanks!

EDIT# I saw how I can download the config.ini to poke around. Interesting it says no dns or ip even though it's dhcp and I can successfully query DNS. I set those manually but still not working. 

EDIT#2 Still troubleshooting. My pfsense box sends smtp notifications with no issue using this config. I try to match it up with APC but still no luck.

<smtp>
<ipaddress>192.168.1.35</ipaddress>
<port>465</port>
<sslvalidate>disabled</sslvalidate>
<timeout></timeout>
<notifyemailaddress>removed@gmail.com</notifyemailaddress>
<username><![CDATA[notifications@removed.net]]></username>
<authentication_mechanism>PLAIN</authentication_mechanism>
<fromaddress>notifications@removed.net</fromaddress>
<password><![CDATA[passwordnotshown]]></password>
<ssl></ssl>