Hi there, I'm having issues with getting sender_dependent_relayhost_maps to work (Rocky Linux 8, postfix v3.5.8). No matter what I try, it seems that the sender_dependent_relayhost_maps is being ignored.
Here's my main.cf: alias_database = hash:/etc/aliases alias_maps = hash:/etc/aliases command_directory = /usr/sbin compatibility_level = 2 daemon_directory = /usr/libexec/postfix data_directory = /var/lib/postfix debugger_command = PATH=/bin:/usr/bin:/usr/local/bin:/usr/X11R6/bin ddd $daemon_directory/$process_name $process_id & sleep 5 debug_peer_level = 2 html_directory = no inet_interfaces = localhost inet_protocols = all mail_owner = postfix mailq_path = /usr/bin/mailq.postfix manpage_directory = /usr/share/man meta_directory = /etc/postfix milter_default_action = accept mydestination = $myhostname, localhost.$mydomain, localhost newaliases_path = /usr/bin/newaliases.postfix non_smtpd_milters = $smtpd_milters queue_directory = /var/spool/postfix readme_directory = /usr/share/doc/postfix/README_FILES sample_directory = /usr/share/doc/postfix/samples sender_dependent_relayhost_maps = hash:/etc/postfix/relayhost_maps sendmail_path = /usr/sbin/sendmail.postfix setgid_group = postdrop shlib_directory = /usr/lib64/postfix smtp_sasl_auth_enable = yes smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd smtp_sasl_security_options = noanonymous smtp_sender_dependent_authentication = yes smtp_tls_CAfile = /etc/pki/tls/certs/ca-bundle.crt smtp_tls_CApath = /etc/pki/tls/certs smtp_tls_security_level = may smtpd_milters = inet:localhost:8891 smtpd_tls_cert_file = /etc/pki/tls/certs/postfix.pem smtpd_tls_key_file = /etc/pki/tls/private/postfix.key smtpd_tls_security_level = may unknown_local_recipient_reject_code = 550 Here's /etc/postfix/relayhost_maps: t...@example.com [smtp.office365.com]:587 And /etc/postfix/sasl_passwd: [smtp.office365.com]:587 t...@example.com:mypasswd Followed by running 'postmap' on each. /etc/postfix/relayhost_maps and /etc/postfix/sasl_passwd are owned by root:root and are 600 (the .db files are 644). Postfix is also then restarted. But if I do a 'echo |mailx -s "Test" -r "t...@example.com" m...@example.com', it's delivered normally, seemingly ignoring the smtp_sender_dependent_authentication directive and the mapping to send through smtp.office365.com. Unless the way I'm testing isn't the right way? I've tried so many different iterations but I'm at a loss at this point. There's nothing in syslog that provides any leads. Any help would be GREATLY appreciated! Thank you!
