After several frustrating hours failing to get Outlook 2003 to login to my dovecot IMAP server on Ubuntu, I finally found the problem. Since I could not find a solution on the net, I thought I'd record it here for posterity.

Symptom:

The symptom was a "Fail" message from Outlook that it was unable to download Inbox (null). Also that it failed to connect. If the problem persists contact your ISP. Error (0x800CCC0E). Or some such combination.

Solution:

When setting up the account in Outlook, *do not* check the box that says "Log on using Secure Password Authentication."

Instead go to "More Settings", then the "Advanced" tab, then check the "This server requires an encrypted connection (SSL)". I checked it for both my incoming and outgoing servers since both are set up to use TLS/SSL.

The problems were all on the client side.

I hope this helps someone else sometime with the same problem.

Regards,

Dan

Thanks Dan!