Port 25 works - 587 Does not SMTP

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NUWELLEPIC

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So we are setting up an on premise server. We are relaying email to our Mail Enable server. If I un-check TLS/SSL and dont use a user name or password, mail is sent from 3CX. Fine, that is expected.

If I check TLS/SSL, I get a message that the operation was cancelled. I get this with or without authentication.

I setup an SMTP relay on the same windows box that runs 3CX and I can get email to relay just fine but when I send an invite, I get the following error. "smtp;554 5.6.1 Body type not supported by Remote Host"

My research indicates the SMTP relay server doesn't like the HTML.

I see a lot of people having success with Gmail Relay but I really dont want to go that route.

I am ready to go out and play in traffic unless someone else has some ideas.
 
I'm not clear on the issue.
Are you trying to use a "format" that is not supported by your SMTP server, yet expecting it to work?
 
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