Hi, I posted a message a few days ago, and still haven't been able to figure this out. I believe this is a result of the certificate having multiple DNS names and my TLS configuration not properly supporting that. Could that be the case?
Aug 6 09:44:20 smtp01 postfix/smtp[24772]: setting up TLS connection to mail.messaging.microsoft.com Aug 6 09:44:20 smtp01 postfix/smtp[24772]: Peer verification: CommonName in certificate does not match: mail.global.frontbridge.com != mail.messaging.microsoft.com Aug 6 09:44:20 smtp01 postfix/smtp[24772]: TLS connection established to mail.messaging.microsoft.com: TLSv1 with cipher RC4-SHA (128/128 bits) Aug 6 09:44:20 smtp01 postfix/smtp[24772]: 03C221880003: to=<t...@example1.com>, relay=mail.messaging.microsoft.com[65.55.88.22], delay=1, status=deferred (TLS-failure: Could not verify certificate) Apparently within the certificate are multiple alternative names, and my postfix configuration is unable to properly handle that. How can I troubleshoot this? This is an older version of postfix, and require forced TLS with certificate validation. Thanks, Alex