welcome to 1996
i’m only seven years late to the party, but i’ve finally set up all my mail handling to go through imap. specifically, the dovecot server, using mutt on the client, and ilohamail for web-based mail. pound provides the ssl front-end for apache.
the next steps are setting up smtp auth and creating my own certificate authority so i install it on my mac (soon to be macs) and avoid various annoying warning dialogs.
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I setup a CA with TinyCA, it works quite well. If you just want a signed certificate, then I'd be happy to sign it with my CA.