Hi, Postfix is giving me a very unhelpful message of just "SASL plain authentication failed:".
So I'm clueless as to where to start troubleshooting. Dovecot config is as follows (I have tried both tcp and socket, both return the same vague error) : ssl = no service auth { unix_listener /var/spool/postfix/private/dovecot-auth { mode = 0660 user = postfix group = postfix } inet_listener { address=127.0.0.1 port=7425 } inet_listener { address=::1 port=7425 } } postconf -n is below: Postconf -n alias_database = alias_maps = authorized_submit_users = compatibility_level = 2 config_directory = /etc/postfix-authrelay data_directory = /var/lib/postfix-authrelay debugger_command = PATH=/bin:/usr/bin:/usr/local/bin:/usr/X11R6/bin ddd $daemon_directory/$process_name $process_id & sleep 5 disable_vrfy_command = yes inet_interfaces = # REMOVED FOR SECURITY inet_protocols = all local_recipient_maps = local_transport = error:5.1.1 Mailbox unavailable mail_owner = postfix mailq_path = /usr/bin/mailq message_size_limit = 20480000 milter_default_action = accept milter_mail_macros = i {auth_type} {auth_authen} {auth_author} {mail_addr} {mail_host} {mail_mailer} milter_protocol = 6 multi_instance_enable = yes multi_instance_group = mta multi_instance_name = postfix-authrelay mydestination = mydomain = # REMOVED FOR SECURITY myhostname = # REMOVED FOR SECURITY mynetworks = # REMOVED FOR SECURITY myorigin = $mydomain newaliases_path = /usr/bin/newaliases non_smtpd_milters = inet:localhost:8891 parent_domain_matches_subdomains = queue_directory = /var/spool/postfix-authrelay relay_domains = sendmail_path = /usr/sbin/sendmail setgid_group = postdrop smtp_bind_address = # REMOVED FOR SECURITY smtp_bind_address6 = # REMOVED FOR SECURITY smtp_sasl_auth_enable = no smtpd_banner = $myhostname ESMTP smtpd_milters = inet:localhost:8891 smtpd_recipient_restrictions = permit_mynetworks,permit_sasl_authenticated,reject_unauth_destination smtpd_relay_restrictions = permit_mynetworks,permit_sasl_authenticated,reject_unauth_destination smtpd_sasl_auth_enable = yes smtpd_sasl_local_domain = $myhostname smtpd_sasl_path = inet:127.0.0.1:7425 smtpd_sasl_security_options = noanonymous,noplaintext smtpd_sasl_tls_security_options = noanonymous smtpd_sasl_type = dovecot smtpd_tls_auth_only = yes smtpd_tls_cert_file = /etc/foobar/ssl/certbot.pem smtpd_tls_dh1024_param_file = ${config_directory}/ssl_certs/dh2048.pem smtpd_tls_dh512_param_file = ${config_directory}/ssl_certs/dh512.pem smtpd_tls_eecdh_grade = strong smtpd_tls_key_file = /etc/foobar/ssl/certbot.key smtpd_tls_mandatory_ciphers = high smtpd_tls_mandatory_protocols = TLSv1.2,!TLSv1.1, !TLSv1, !SSLv2, !SSLv3 smtpd_tls_security_level = encrypt tls_eecdh_strong_curve = prime256v1 tls_preempt_cipherlist = yes unknown_local_recipient_reject_code = 550