[ ... ] However, I can't seem to figure out how to configure OE to use SSL.
You would do better to ask this question on a Microsoft list; it has nothing to do with FreeBSD. That being said, sufficiently recent versions of Outlook Express will have an "Advanced" tab in the account properties inspector for a particular mail account which contains port numbers for "Outgoing mail (SMTP)", and then a checkbox marked "This server requires a secure connection (SSL)".
-- -Chuck
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