I got this working -- in the midst of the different iterations, I had
a mismatch in domains in sasl_passwd and relayhost_maps.  Once those
have been aligned, it's working as expected.

Thanks!

On Wed, Nov 9, 2022 at 1:20 PM Bryan Arenal <b.are...@gmail.com> wrote:
>
> 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!

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