Running 10.5.7 and Mail 3.6. I've checked the "use SSL" checkbox in the preferences. Does Mail always use SSL, or are there circumstances where it may try to revert to an insecure connection?
I won't pretend to be an expert, but I'm pretty sure if you've checked that box it won't revert to an unencrypted connection regardless. Though if your mail server only accepts SSL connections that wouldn't be an option anyway.