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View Full Version : Secure SMTP with Microsoft Outlook 2003


andieveritt
01-10-2006, 10:03 PM
I've been fighting this for about a week so thought I would post a message about just in case it saves someone else going through the same issues.

I wanted to setup mail with secure IMAP and authenticated SMTP, between these forums and a bit of trusty Google I got the VPS (RHEL4) all configured. Everything looked fine on the server but my Outlook 2003 client would only send mail about 20% of the time, the rest of the time it reported an error like 'Error Number: 0x800CCC0F' complaining that the server didn't support SSL. I installed Thunderbird and it worked reliably from the start - big giveway that it was something Outlook related!

Next clue was a number of articles about issues with Norton anti-virus - it doesn't support secure SMTP so I had to turn off scanning for outbound messages -- but this didn't resolve things :(.

In the end I found a couple of articles pointing me in the right direction. Outlook 2003 SR1 has a bug which prevents it from making SSL connections on non-standard ports reliably. As I was using port 587 I was hitting this problem. Switching to port 25 for outbound SMTP solved the problem. I have now upgraded to Outlook 2003 SR2 and it works fine on any port (that I tried).