Notifications to non-STARTTLS port stopped working after upgrade to 2.2
It appears that the behavior change was from 2.1 to 2.2. I noticed that in 2.2 both 'Enable SMTP over SSL/TLS'
and 'Enable STARTTLS' is now set. 'Enable STARTTLS' is greyed out when 'Enable SMTP over SSL/TLS' is checked but it still allows 'Enable STARTTLS' to be set. I didn't modify this before the upgrade and it was working before on 2.1 so I am uncertain why the behavior change.
May 30 10:33:40 php: sendmail: Could not send the message to firstname.lastname@example.org – Error: 454 4.3.3 TLS not available after start
I am using port 465 where STARTTLS is not supported on our mail server.
To fix it I unchecked 'Enable SMTP over SSL/TLS' so that I could uncheck 'Enable SMTP over SSL/TLS'. After unchecking 'Enable SMTP over SSL/TLS' and saving I was then able to get emails.