I got it! The problem was that Courier was configured to use its own self-signed certificate (set up for "localhost"), and because I was connecting to IMAP using the same hostname I guess Mail.app was bailing out the SMTP connection because the certificate didn't match the one from before.

Thanks for all the help, I learned a bunch going through this process!

-Dan


On Oct 19, 2008, at 2:09 PM, Noel Jones wrote:

mouss wrote:
Dan Phiffer a écrit :
One thing I should have specified in my last message is that I still
can't send email using SMTP over SSL. Mail.app behaves exactly the same
as before and I'm still seeing "SSL_accept error" in mail.log.

I suggest regenarting the certificate and setting the CN to the mail
server name (mail.gridfilter.com), instead of your name.

While that is correct, since it's a self-signed certificate it won't verify anyway.

Set smtpd_tls_loglevel to 0 or 1 to suppress unimportant/unrelated messages.

Looks to me as if TLS is working correctly - using openssl s_client OP was able to connect and communicate with the server. Since s_client works, I'm inclined to think any further problems are with Mail.app configuration. I'm not familiar with Mail.app; maybe it wants STARTTLS support on port 25 or 587 rather than the deprecated wrappermode on 465, or maybe it reacts badly to the mismatched name.

--
Noel Jones


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