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