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Connecting to Exchange 2003 over port 465

By wstclair33 ·
I am running Exchange server 2003 I have a front end server that sits in my DMZ, and a back end server on my internal network. All incoming and outgoing mail is routed through my front end server.

On the front end server I have two virtual smtp servers configured one the default that all outgoing and incoming mail are routed through using port 25.

The second smtp server I have configured for secure access for users who are off site and want to connect to their accounts securely. I have smtpS (port 465) configured on this smtp server. I configure my Outlook Express client to use ssl over port 465 connecting to this server but I then get an error message saying:

"Your server has unexpectedly terminated the connection. Possible causes for this include server problems, network problems, or a long period of inactivity. Account "KCG", Server "Servername", Protocold: SMTP, Port 465, Secure(SSL): Yes, Error Number: 0x800CCC0F"

When trying to send mail over port 465. I can send over port 25 with no problems.

I can telnet and connect to this server over port 465, but when I try to send mail from the command line I get the following error:

530 5.7.0 Must issue a STARTTLS command first

Has anyone seen this issue? Any help would be great!!


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