OK, I did not know that this user has a new computer with Outlook 2010.
This SHOULD make it easier but...
I have the computer right next to me, they brought it over. It is on the same LAN as this notebook. I can access my server with:
openssl s_client -connect z9m9z.htt-consult.com:995
And then log the user in with the appropriate POP3 credentials.
In Outlook 2010, in Advanced settings I have specified "This server requires an encrypted connection (SSL)" and it switches to port 995 (from 110). I try connecting and I get an error that
"Your server does notg support the connection encryption type you have specified."
The first time we tried this it installed my self-signed cert in the local cert store.
Any idea on what is going on or how to get this working?