Hello,
# certificate pki mail_cert cert "/etc/letsencrypt/live/***/fullchain.pem" pki mail_cert key "/etc/ssl/private/server.key"
I don't know which system has this paths. But it looks wrong to me. Are you sure the server-key isn't in "/etc/letsencrypt/live/***/"?
Which acme-client do you use?
Any idea on what could the reason be?
The config looks ok. Test the following: Stop the smtpd daemon: # rcctl stop stmpd Start smtpd in the foreground: # smtpd -d Send a testmail: $ sendmail username abcd test Ctrl+d Post the output of smtpd.