How to send email to a SMTP server over a secure channel using STARTTLS setting of a send connector (Exchange and SMTP server are in the same domain)

I’m trying to send email using exchange send connector STARTTLS setting to the SMTP server. I have read multiple documents on configuring TLS for send connector, but they talks about outbound connections to internet facing servers. My Exchange 2013 and SMTP
server is in the same domain (let’s say A.com) and I’m creating dummy domains on my SMTP server (e.g.
[email protected],
[email protected] ) and their respective send connectors on the exchange server end. In the smart host section added the IP address of the SMTP server and in the scoping section added the SMTP domain address (e.g. dummy1.local ). In the FQDN field, added
the FQDN of the exchange server 2013 which certificate is enabled with SMTP service.
Could you tell me a step by step procedure, where I’m going wrong or any extra settings needs to added?
Presently, it is giving me an error that 530 5.5.1 TLS encrypted connection is required.
Note: I’ve created the Microsoft CA certificates for the SMTP and exchange servers and imported them in the personal certificate container. In which, the exchange certificate is created with FQDN name of the server and enabled for the SMTP service.
I’m using OPENSSL certificate for making the SMTP server TLS enabled. (let me know, if I need to import the OPENSSL certificate anywhere on the exchange end)?
Thanks!

-IgnoreSTARTTLS is set to false on the send connector properties.
I'm trying to established a HTTP over TLS connection. I'm not using mutual TLS between these two server.
The send connector protocol logging is attached as below,
2014-09-22T20:09:45.468Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,2,10.219.3.74:24939,10.219.3.73:25,<,220 SMTP.A.local Welcome (MTA version),
2014-09-22T20:09:45.546Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,3,10.219.3.74:24939,10.219.3.73:25,>,EHLO Exchange.A.local,
2014-09-22T20:09:45.624Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,4,10.219.3.74:24939,10.219.3.73:25,<,250-SMTP.A.local Exchange.A.local OK,
2014-09-22T20:09:45.624Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,5,10.219.3.74:24939,10.219.3.73:25,<,250-SIZE,
2014-09-22T20:09:45.624Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,6,10.219.3.74:24939,10.219.3.73:25,<,250-8BITMIME,
2014-09-22T20:09:45.624Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,7,10.219.3.74:24939,10.219.3.73:25,<,250-BINARYMIME,
2014-09-22T20:09:45.624Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,8,10.219.3.74:24939,10.219.3.73:25,<,250-PIPELINING,
2014-09-22T20:09:45.624Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,9,10.219.3.74:24939,10.219.3.73:25,<,250-HELP,
2014-09-22T20:09:45.624Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,10,10.219.3.74:24939,10.219.3.73:25,<,250-DSN,
2014-09-22T20:09:45.624Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,11,10.219.3.74:24939,10.219.3.73:25,<,250-CHUNKING,
2014-09-22T20:09:45.624Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,12,10.219.3.74:24939,10.219.3.73:25,<,250-AUTH SCRAM-SHA-1 GSS-SPNEGO DIGEST-MD5 CRAM-MD5 NTLM,
2014-09-22T20:09:45.624Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,13,10.219.3.74:24939,10.219.3.73:25,<,250-AUTH=SCRAM-SHA-1 GSS-SPNEGO DIGEST-MD5 CRAM-MD5 NTLM,
2014-09-22T20:09:45.624Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,14,10.219.3.74:24939,10.219.3.73:25,<,250-STARTTLS,
2014-09-22T20:09:45.624Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,15,10.219.3.74:24939,10.219.3.73:25,<,250-DELIVERBY,
2014-09-22T20:09:45.624Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,16,10.219.3.74:24939,10.219.3.73:25,<,250-MT-PRIORITY,
2014-09-22T20:09:45.640Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,17,10.219.3.74:24939,10.219.3.73:25,<,250 ENHANCEDSTATUSCODES,
2014-09-22T20:09:45.655Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,18,10.219.3.74:24939,10.219.3.73:25,>,STARTTLS,
2014-09-22T20:09:45.671Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,19,10.219.3.74:24939,10.219.3.73:25,<,220 2.7.0 Ready to start TLS,
2014-09-22T20:09:45.687Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,20,10.219.3.74:24939,10.219.3.73:25,*,,Sending certificate
2014-09-22T20:09:45.687Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,21,10.219.3.74:24939,10.219.3.73:25,*,CN=Exchange.A.local,Certificate subject
2014-09-22T20:09:45.687Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,22,10.219.3.74:24939,10.219.3.73:25,*,"CN=DC-CA, DC=A, DC=local",Certificate issuer name
2014-09-22T20:09:45.687Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,23,10.219.3.74:24939,10.219.3.73:25,*,63E7E70100000000000B,Certificate serial number
2014-09-22T20:09:45.687Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,24,10.219.3.74:24939,10.219.3.73:25,*,CAEB1200CDF49715E5F2E4B8315EFDDC01F8F945,Certificate thumbprint
2014-09-22T20:09:45.780Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,25,10.219.3.74:24939,10.219.3.73:25,*,Exchange.A.local,Certificate alternate names
2014-09-22T20:09:46.654Z,Exchange-SMTP send connector,08D1A4A14C7EDED5,26,10.219.3.74:24939,10.219.3.73:25,-,,Local
2014-09-22T20:09:46.669Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,0,,10.219.3.73:25,*,,attempting to connect
2014-09-22T20:09:46.685Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,1,10.219.3.74:24940,10.219.3.73:25,+,,
2014-09-22T20:09:46.701Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,2,10.219.3.74:24940,10.219.3.73:25,<,220 SMTP.A.local Welcome (MTA version),
2014-09-22T20:09:46.701Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,3,10.219.3.74:24940,10.219.3.73:25,>,EHLO Exchange.A.local,
2014-09-22T20:09:46.716Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,4,10.219.3.74:24940,10.219.3.73:25,<,250-SMTP.A.local Exchange.A.local OK,
2014-09-22T20:09:46.716Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,5,10.219.3.74:24940,10.219.3.73:25,<,250-SIZE,
2014-09-22T20:09:46.716Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,6,10.219.3.74:24940,10.219.3.73:25,<,250-8BITMIME,
2014-09-22T20:09:46.716Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,7,10.219.3.74:24940,10.219.3.73:25,<,250-BINARYMIME,
2014-09-22T20:09:46.716Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,8,10.219.3.74:24940,10.219.3.73:25,<,250-PIPELINING,
2014-09-22T20:09:46.716Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,9,10.219.3.74:24940,10.219.3.73:25,<,250-HELP,
2014-09-22T20:09:46.716Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,10,10.219.3.74:24940,10.219.3.73:25,<,250-DSN,
2014-09-22T20:09:46.716Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,11,10.219.3.74:24940,10.219.3.73:25,<,250-CHUNKING,
2014-09-22T20:09:46.716Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,12,10.219.3.74:24940,10.219.3.73:25,<,250-AUTH SCRAM-SHA-1 GSS-SPNEGO DIGEST-MD5 CRAM-MD5 NTLM,
2014-09-22T20:09:46.716Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,13,10.219.3.74:24940,10.219.3.73:25,<,250-AUTH=SCRAM-SHA-1 GSS-SPNEGO DIGEST-MD5 CRAM-MD5 NTLM,
2014-09-22T20:09:46.716Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,14,10.219.3.74:24940,10.219.3.73:25,<,250-STARTTLS,
2014-09-22T20:09:46.732Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,15,10.219.3.74:24940,10.219.3.73:25,<,250-DELIVERBY,
2014-09-22T20:09:46.732Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,16,10.219.3.74:24940,10.219.3.73:25,<,250-MT-PRIORITY,
2014-09-22T20:09:46.732Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,17,10.219.3.74:24940,10.219.3.73:25,<,250 ENHANCEDSTATUSCODES,
2014-09-22T20:09:46.810Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,18,10.219.3.74:24940,10.219.3.73:25,*,,sending message with RecordId 52652004081667 and InternetMessageId <[email protected]>
2014-09-22T20:09:46.810Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,19,10.219.3.74:24940,10.219.3.73:25,>,MAIL FROM:<> SIZE=7653 BODY=BINARYMIME,
2014-09-22T20:09:46.810Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,20,10.219.3.74:24940,10.219.3.73:25,>,RCPT TO:<[email protected]>,
2014-09-22T20:09:46.825Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,21,10.219.3.74:24940,10.219.3.73:25,<,530 5.5.1 A TLS-encrypted connection is required,
2014-09-22T20:09:46.950Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,22,10.219.3.74:24940,10.219.3.73:25,<,503 5.5.1 unexpected RCPT command,
2014-09-22T20:09:46.981Z,Exchange-SMTP send connector,08D1A4A14C7EDED6,23,10.219.3.74:24940,10.219.3.73:25,>,RSET,

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