What do your qmail smtpd logs say?
From: Jeff Koch [mailto:jeffk...@intersessions.com]
Sent: Tuesday, June 16, 2009 7:58 AM
To: toaster@shupp.org
Subject: [toaster] SMTP TLS with Outlook problem
We're having a hard time getting SMTP TLS to work with Outlook and
Windows Mail (Vista). The mail server checks out fine when we execute:
openssl s_client -crlf -starttls smtp -connect localhost:25
either locally or from another linux server. However, our PC's and
customer PC's just show sending errors. These PC's can send mail just
fine using a non-SSL connection.
Any help would be appreciated.
Best Regards,
Jeff Koch