I was getting some relay issues when my local IP changed so I realized or thought that perhaps my SASL wasn’t working
I did a bunch of tweaking which is never good but when i switched my mail to port 587 i was able to once again send with no problem BUT when i did the telnet test froth postfix.org <http://postfix.org/> as follow 220 tuna.theoceanwindow-bv.com ESMTP EHL0 502 5.5.2 Error: command not recognized EHLO 501 Syntax: EHLO hostname EHLO KASDIVI.COM 250-tuna.theoceanwindow-bv.com 250-PIPELINING 250-SIZE 10240000 250-ETRN 250-STARTTLS 250-AUTH PLAIN LOGIN 250-ENHANCEDSTATUSCODES 250-8BITMIME 250 DSN AUTH PLAIN base64 gibberish 535 5.7.8 Error: authentication failed: the base 64 encodes (\0user\@doman.com <http://doman.com/>\0Password) I also tried (\0user\@doman\.com <http://doman.com/>\0Password) I am running postfix 2.12-20140709 Dovecot version 1.2.17 Postconf -n is as follows body_checks = regexp:/usr/local/etc/postfix/body_check bounce_size_limit = 50000 command_directory = /usr/local/sbin config_directory = /usr/local/etc/postfix content_filter = smtp-amavis:[127.0.0.1]:10024 daemon_directory = /usr/local/libexec/postfix daemon_timeout = 36000s data_directory = /var/db/postfix debugger_command = PATH=/bin:/usr/bin:/usr/local/bin:/usr/X11R6/bin xxgdb $daemon_directory/$process_name $process_id & sleep 5 delay_warning_time = 2h disable_vrfy_command = yes header_checks = regexp:/usr/local/etc/postfix/header_checks home_mailbox = Maildir/ html_directory = /usr/local/share/doc/postfix inet_protocols = ipv4 mail_owner = postfix mail_spool_directory = /var/mail/vmail mailq_path = /usr/local/bin/mailq manpage_directory = /usr/local/man maps_rbl_domains = bl.spamcop.net mydestination = localhost.$mydomain, localhost mydomain = theoceanwindow-bv.com mynetworks = 127.0.0.0/32, 127.0.0.1,209.160.65.133, 209.160.68.112, kasdivi.is-a-geek.com, webmail.kasdivi.com,bowmasair.com, hsd1.nj.comcast.net myorigin = $mydomain newaliases_path = /usr/local/bin/newaliases queue_directory = /var/spool/postfix readme_directory = /usr/local/share/doc/postfix recipient_bcc_maps = hash:/usr/local/etc/postfix/recipient_bcc relay_recipient_maps = hash:/usr/local/etc/postfix/relay_recipients sample_directory = /usr/local/etc/postfix sendmail_path = /usr/local/sbin/sendmail setgid_group = maildrop slow_destination_concurrency_failed_cohort_limit = 10 slow_destination_concurrency_limit = 1 slow_initial_destination_concurrency = 1 smtp_tls_note_starttls_offer = yes smtpd_banner = $myhostname ESMTP smtpd_delay_reject = yes smtpd_helo_required = yes smtpd_helo_restrictions = permit_sasl_authenticated,check_helo_access hash:/usr/local/etc/postfix/helo_access,reject_invalid_hostname,permit smtpd_recipient_restrictions = permit_mynetworks, check_sender_access pcre://usr/local/etc/postfix/sender_access reject_rhsbl_sender fresh.spameatingmonkey.net, reject_unauth_destination, check_client_access hash:/usr/local/etc/postfix/rbl_override, reject_rbl_client zen.spamhaus.org, reject_rbl_client bl.spam, reject_rbl_client bl.spameatingmonkey.net, reject_rhsbl_client fresh.spameatingmonkey.net, reject_rhsbl_sender urired.spameatingmonkey.net,permit_sasl_authenticated smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated reject smtpd_sasl_auth_enable = yes smtpd_sasl_path = private/auth smtpd_sasl_type = dovecot smtpd_sender_restrictions = permit_sasl_authenticated, reject_unknown_sender_domain, reject_unauthenticated_sender_login_mismatch, check_sender_access pcre://usr/local/etc/postfix/sender_access permit_mynetworks smtpd_tls_CAfile = /usr/local/etc/keys/root.crt smtpd_tls_cert_file = /usr/local/etc/keys/server.cert smtpd_tls_key_file = /usr/local/etc/keys/private.key smtpd_tls_loglevel = 3 smtpd_tls_received_header = yes smtpd_tls_security_level = may smtpd_tls_session_cache_timeout = 3600s tls_random_source = dev:/dev/urandom transport_maps = hash:/usr/local/etc/postfix/transport unknown_local_recipient_reject_code = 550 virtual_alias_maps = hash:/usr/local/etc/postfix/virtual virtual_gid_maps = static:1000 virtual_mailbox_base = /var/mail/vmail virtual_mailbox_domains = hash:/usr/local/etc/postfix/virtual_domains virtual_mailbox_maps = hash:/usr/local/etc/postfix/virtual_mailbox virtual_minimum_uid = 100 virtual_uid_maps = static:1003 I AM sending mail through the SMTP server so maybe I should just leave it alone ?? Any insights or suggestions of point out dumb errors would be appreciate