Looking for some troubleshooting assistance with the notifiers.

So about 3 months ago Simon stopped sending emails to us ... I wasn't sure what changed, but I figured it was something with the computer. So I ran a simple test and opened Apple Mail and sent out an email from there and the email sent out just fine. At this point I figured something with Simon and since I was planning on upgrading from Mavericks with Simon 3.xx to El Capitan running Simon 4 soon, I figured I'd wait and start completely fresh.

Well, that's done.

I formatted the HDD and installed a fresh copy of OS X 10.11.3 and then I installed Simon 4.1.1 and I didn't import over ANY files whatsoever. Everything is setup fresh, by hand.

Low and behold, exact same issue!

Without this becoming a wall of text, I'll try to explain my troubleshooting techniques thus far:
I first opened Terminal and issued the following commands:

sendmail emailaddress@recipient.com
Subject: This is a test from terminal

This is the content of the message.
.

This shows up in the mail.log file:
Jan 29 15:27:38 Simon-Offsite postfix/smtp[9727]: 6E9EEA332A: to=, relay=none, delay=168, delays=17/0.02/151/0, dsn=4.4.1, status=deferred (connect to mx6.mail.icloud.com[17.133.229.12]:25: Operation timed out)

All right, I figured this is probably happening because the of the Internet Service Provider not allowing sending without authentication.

So then I tried Apple Mail, setup an account (same settings as what I use in Simon), and works, no problem.

SO then I tried having Simon using Apple Mail. Notify Now ⌘K still doesn't work, but then out of no where I got a Recovery email on one of my tests that I set up. I looked at Apple Mail Sent Items and sure enough it's in there. Why did that work but Notify Now ⌘K not? Either way, this isn't what I want, I want Simon to be it's own service and not rely on another program.

So I setup another mail server of which I can view the logs on. I click Notify Now ⌘K .... nothing Simon doesn't even attempt to connect to the mail server to even log on. So then (thinking maybe Notify Now ⌘K is completely broken in Simon 4.1.1) I try making a test fail since I got an email from that the last time when using Apple Mail. Again, nothing at all.

So I went to the firewall on the network with the mail server and looked for packets coming in from this Simon machine ... nothing at all is coming to my network.

Is DNS working?

Terminal command: host mail.myserver.com
mail.myserver.com has address xxx.xxx.xxx.xxx

It's right.

So my question here is, is there a log that Simon writes to for emails that it attempts to send?

I'd like to see if Simon is running into an error with the network / ISP / whatever.

Or other, if the idea is present, are there other things I could try / test to eliminate?

Thanks for any help possible.