Database mail is not sending mail through SMTP TLS

Hello,
I have strange issue with SQL 2012 and Database mail. For some reason server refusing to send email over SMTP TLS. The only error reported to log is below which is completely useless (shame on you Microsoft for that).
I verified that there
1. No networking issues between server and SMTP relay host (Installed Windows Mail and sent mail through it)
2. That account and password is right (verification same as above)
3. That mail engine itself is working (verified through plain SMTP relay through local box itself)
I made a network capture of the process as well and it showing SQL server making initial TLS connection successfully to SMTP relay box and then never sending any data over established TCP connection and eventually timinig out after 60s with no data being
sent).
Any ideas?
Date 1/4/2015 2:03:33 AM
Log Database Mail (Database Mail Log)
Log ID 268
Process ID 223804
Mail Item ID 125
Last Modified 1/4/2015 2:03:33 AM
Last Modified By sa
Message
The mail could not be sent to the recipients because of the mail server failure. (Sending Mail using Account 2 (2015-01-04T02:03:33). Exception Message: Cannot send mails to mail server. (Failure sending mail.).

I looked at both locations mentioned and there is nothing there to tell exactly what is the problem. Again I see on network capture that connection IS established, just no data is being sent.
Relay is done through AWS relay server so there is not an issue on their side. Again I tested this scenario via Windows Mail client installed directly on SQL server, so any issues on the other side (like connectivity, timeouts, AV interferences are ruled
out since Windows Mail works).
Email error log supposed to have details about failure in last brackets, the one which in my case contains fuzzy "Failure to send mail". It supposed to say "unable to establish connection", "timeout expired" etc if there were
any issues on the other side. I have found a lot of reports of those issues on this forum where issue is explicitly stated in error message. In my case there is ZERO information about the issue. Mark Russinovich has excellent presentations where he talks about
useless error messages and this is certainly one of them.
Failure sending mail.

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