I think I’ve finally accomplished it. It being getting my mail server to use SSL for IMAP/POP/SMTP.
I’m running Leopard Server on an Intel Mac mini and I’ve been screwing around with Keychain Access > Certificate Assistant for the past 2 days. Don’t waste your time.
Joel Rennich has some [excellent instructions on getting everything up and running][ssl]. The instructions were written with Panther in mind but it worked almost perfectly.
The almost is that I couldn’t write the “01” to the demoCA/serial file so I opened it up in pico and added the value from there.