So I have a queue of 3 emails to send, via MS outlook smtp.
All 3 will send fine.
At a later time, 2 will send and I get this in server output:
Email was not sent due to exception javax.mail.MessagingException Could not convert socket to TLS
Sure enough, that 3rd email was not sent. It is not in the outlook Sent or draft folder. I think its still on the server unsent by Aware. But why?
... but eventually it will go out.
From the server output tab: The next time aware did this: "Sending unsent email..."
my email (after throwing the obligatory 'Incorrect header check' warning) was sent.
Do we know Aware is using TLSv1.2 now?
Stack overflow thread here.