Thanks all for the help. Today I installed courier-imap, and reconfigured Exim for Maildir delivery, and I can now get mail out over POP3 + SSL. Apple's OS X mail client and Mac Eudora 6b are working fine. (I had sort of been wanting to try maildirs, and this way I can evolve to IMAP if I want, so I will probably stick with this.)
Eudora for Windows is still hosed though. I did manually add my cert to the trusted list but I still have this error to deal with:
SSL Negotiation Failed: Certificate bad: Destination Host name does not match host name in certificate Cause (-6984)
Now, I am using a self-signed cert that I created with courier's shortcut command, and this test system does not have a real hostname yet, which seems like it would explain this error... but does anyone know a way to tell Eudora to not care about bad certificates? Or better still, how do I create a cert myself that satisfies Eudora? Will it even be possible to when my mail server testbed is at 192.168.x.y, without a fully-qualified hostname?
Getting real close now though, thanks to everyone!
- Matt
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