I am working on having a postfix server relay certain messages via another server instead of delivering normally. My issue that I can't figure out is trying to get postfix to authenticate with another mail server (no tls). If the other server is listening on seemingly any other port than 25, the auth works normally and the message goes thru. When postfix trys to send to a relay host on port 25 though, it never even tries to authenticate and relaying fails. I am working with postfix 2.3.3 on centos 5.7 BTW. (both machines in play here are vm's so I won't mask any of the config)

The server I am sending to (under my control) always replies to an ehlo the same way (no matter what port I tell it to listen on) with:

Escape character is '^]'.
220 test.test
ehlo sdfgsdfg
250-test.test
250-PIPELINING
250-SIZE 30240000
250-ETRN
250-STARTTLS
250-AUTH PLAIN LOGIN
250-AUTH=PLAIN LOGIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN


Postfix Config:  (the one that needs to relay to another machine)
root@test /etc/postfix # postconf -n
alias_database = hash:/etc/aliases
alias_maps = hash:/etc/aliases
command_directory = /usr/sbin
config_directory = /etc/postfix
daemon_directory = /usr/libexec/postfix
debug_peer_level = 2
debug_peer_list = 10.10.10.5
html_directory = no
inet_interfaces = localhost
mail_owner = postfix
mailq_path = /usr/bin/mailq.postfix
manpage_directory = /usr/share/man
mydestination = $myhostname, localhost.$mydomain, localhost
mynetworks = 127.0.0.0/8
newaliases_path = /usr/bin/newaliases.postfix
queue_directory = /var/spool/postfix
readme_directory = /usr/share/doc/postfix-2.3.3/README_FILES
sample_directory = /usr/share/doc/postfix-2.3.3/samples
sendmail_path = /usr/sbin/sendmail.postfix
setgid_group = postdrop
smtp_sasl_auth_enable = yes
smtp_sasl_mechanism_filter = plain, login
smtp_sasl_password_maps = static:matt:bigbigger
smtp_sasl_security_options = noanonymous
unknown_local_recipient_reject_code = 550


Am I missing something basic as to why postfix won't try to authenticate on the target server on port 25? (it works awesome on ports 26/27/28/587 so far)

Thanks!
-Matt T

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