So I cannot get the emails working via SMTP, despite trying numerous solutions. At first it was definitely the config on my server, but now I tested a basic PHP mail() function and it sent (and was received) just fine. I was reading on the PHP Mailer wiki (
https://github.com/PHPMailer/PHPMailer/wiki/Troubleshooting) about setting SMTPDebug = 2, to get more info on the "Could not connect to SMTP Host" error. Obviously the mail is being sent via an ajax call, so anytime I try to print info directly from engine/Notifications/Email.php it's not going to work, and setting $mailer->SMTPDebug = 2 in that file didn't work either. Is there anyway I can get some more info out to see what is going wrong for me?
For the record, I'm running it on IIS and am trying to send via a separate mail server that is also on the local network. I know IIS isn't technically supported, but everything has been working perfectly fine up until now (it may as well be listed as supported).