[Mail] Failed to start TLS encryption - SMTP - $50 REWARD TO FIX

[Dyke]

Been working fine for over 3months, I believe I updated my server when this has occurred...the only thing I can think of that has disrupted it. Now it's not sending out the emails, and is displaying the current error:



What do you think this could be related too? Really pulling my hair out on this. I'm using Ubuntu 16.0.4.

---

EDIT: I'm willing to give the person who fixes this $20.