How do I set up Mail service for simple IMAP with SSL?

This should be easy but something isn't working. I have an Xserve with 10.6. I've enabled the Mail service, and want to add this server as an Account under Entourage. I've put in the IP address, my username/password, etc. but something isn't working. It appears under the Accounts folder tree, but when I try to send an email, I have a window that says "4.7.0 TLS not available due to local problem", Error -17099". I've also seen errors telling me the password is being sent in cleartext and I can't see where I enable the same (SSL, password needed) settings on the client and the server menus. Can someone clue me in - what are the right settings on both ends to have a simple IMAP w/o cleartext passwords? I had this working fine in 10.4 Server... Thanks!
Mike

I see dropdown menus for SMTP SSL and IMAP/POP SSL. I have them both set as "Require"
Do not to this if your server is handling incoming mail from outside your network.
Few remote mail servers will use SSL, so if your server requires SSL then you will not be able to receive mail from outside your domain.
'Use', on the other hand, advertises the fact your server supports SSL, so clients and remote servers can use if if they like, but this still allows other mail in.
What should "Authentication" be - "Login" or "Plain"
Do not use Plain unless you absolutely trust all your clients (i.e. they're all on a LAN or all using SSL). Plain sends an unencrypted password over the wire, which is susceptible to sniffing.
what will the client be using?
Whatever you set it to.
The client complains about a correct root certificate not being installed).
Are you using a self-signed certificate? if so, you're going to get that unless you do a lot of extra work. Getting a real certificate from a trusted authority should resolve this.
As for the slow connections, the use of SSL shouldn't significantly impact connection or delivery/transfer times, so something else is amiss.

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