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I am not sure how or why it was set up this way, but it I think that it should have been done differently. HTTPS and SMTP (STARTTLS) are completely different in how the connection is established, and must be handled differently. I think HTTPS should have been included with the S/MIME and SLDAP option, as the three of them operate similarly. SMTP requires additional handshaking before the STARTTLS command can be used.
I would call support and have us open a case and bug for this, as the STARTTLS option it is broken as it is now.
If you want to perform the test, I would find another system and use the following command to verify that a secure connection can be made to the mail server:
openssl s_client -connect <IP Address>:25 -starttls smtp -crlf
I use this command on *nix systems. It can also be done from Windows, but you will need to install the openssl package first.
Bug seems to be a known bug (BugID 663488 I believe).