Web Reference: Apr 21, 2025 · Diagnose and resolve Postfix TLS handshake failures when connecting to an Exchange server. Learn common causes like protocol mismatches, certificate issues, and network problems, with practical troubleshooting steps and configuration tips. Server-side certificate and private key configuration In order to use TLS, the Postfix SMTP server generally needs a certificate and a private key. Both must be in "PEM" format. The private key must not be encrypted, meaning: the key must be accessible without a password. Oct 7, 2020 · I use Postfix in combination with Lets Encrypt to transmit TLS encrypted e-mails. The following parameters in /etc/postfix/main.cf are relevant: smtp_tls_key_file = /etc/letsencrypt/live/foo.bar/pr...
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