So I set up a self-signed SSL certificate for my IMAP email and it went pretty painless. Every time a launch mail.app I have to tell it to trust the cert, but otherwise it runs fine. And Eavesdrop confirms that things are very much encrypted now. I set it to Require SSL in IMAP, since I'm the only end user on this server.
Now I need to set up SSL on SMTP and I'm not sure what to use. As I understand it, SMTP uses SSL for SMTP-to-SMTP connections if it's available. My cert is self signed, so that probably isn't going to work? Is the mail server smart enough to know that if I choose 'Require', that I mean only for mail sent from my client to the SMTP server, and not incoming mail from other SMTP servers to my server?
The main thing I want out of this is to protect my login credentials when I'm connecting to my own mail server from my computers, especially my laptop when I could be sharing a wireless network with anyone.
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