SSL connection failure. Please check host and port settings.

[cpha]

Trying to connect to Exchange Server 2003 using IMAP.

"receiving mail" settings work over SSL on port 993,

However sending email under SMTP using port 465, I get the error message . "SSL connection failure. Please check host and port settings." I have also tried enabling disable TLS / Required SSL on the mail server under SMTP virtual directory and still get this error message. When I uncheck SSL, it defaults to port 25 and works.

I have tried different ports and still get the same error.

Would appreciate any help in this regards and thanks in advance

[phoenix]

Originally Posted by cpha

However sending email under SMTP using port 465, I get the error message . "SSL connection failure. Please check host and port settings." I have also tried enabling disable TLS / Required SSL on the mail server under SMTP virtual directory and still get this error message. When I uncheck SSL, it defaults to port 25 and works.

Does the server support sending mail via Port 465? You may have to ask the Exchange administrator if that's supported.

[cpha]

Originally Posted by phoenix

Does the server support sending mail via Port 465? You may have to ask the Exchange administrator if that's supported.

Yes it does. If i telnet to the mail server on port 465, i was able to send the email.

[phoenix]

Are you sure that it requires SSL on port 465? Have you tried unchecking that and changing the port to see if it works?

[cpha]

Originally Posted by phoenix

Are you sure that it requires SSL on port 465? Have you tried unchecking that and changing the port to see if it works?

Yes. Also i tried changing the port and still have the problem.

From what i understand the incoming IMAP is secured as it uses SSL, all i am trying to do is make sure that when i am sending an email, it is secured using SSL.

I also tried using Mac Mail with IMAP settings and it works.

[ArcaneMagus]

Unless you are somehow able to negotiate an SSL connection by hand, SSL was not enabled on port 465 so I would look into how exactly you are enabling SSL, and how that port is being forwarded to your Exchange server. If you were able to "telnet to the mail server on port 465" and then send mail, my guess would be that port 465 is being forwarded to port 25.

[cpha]

Originally Posted by ArcaneMagus

Unless you are somehow able to negotiate an SSL connection by hand, SSL was not enabled on port 465 so I would look into how exactly you are enabling SSL, and how that port is being forwarded to your Exchange server. If you were able to "telnet to the mail server on port 465" and then send mail, my guess would be that port 465 is being forwarded to port 25.

Not sure what you mean by negotiate by hand ? I have a SSL cert installed on the exchange server. Created a new SMTP Virtual diretory in Exchange server System Management console. Associated the SSL cert on the SSL is how i have configured SSL.

Port 465 is mapped to 25 under the SMTP protocol options.

What do i have to do to select the check box " Use SSL encryption when sending email"?

[cpha]

Originally Posted by ArcaneMagus

Unless you are somehow able to negotiate an SSL connection by hand, SSL was not enabled on port 465 so I would look into how exactly you are enabling SSL, and how that port is being forwarded to your Exchange server. If you were able to "telnet to the mail server on port 465" and then send mail, my guess would be that port 465 is being forwarded to port 25.

Forgot to mention, i did telnet to port 465 and was successful in sending an email to myself.

[ArcaneMagus]

Originally Posted by cpha

Port 465 is mapped to 25 under the SMTP protocol options.

Originally Posted by cpha

i did telnet to port 465 and was successful in sending an email to myself.

What I meant is that if you were able to telnet to port 465 without the connection (almost) instantly being closed then SSL was not enabled on that port as SSL is binary mode only. Being able to telnet to that port and send an email to yourself meant that you were simply forwarding port 465 to port 25, which will never do SSL.

You need to remove that mapping of port 465 to port 25 as it is absolutely wrong. I am not sure exactly how you are supposed to setup SSL on an Exchange server, but XFOR: Enabling SSL For Exchange Server is probably a good place to start, other then Google of course.