FINALLY it worked, but not before i disabled NTLM in the config, because otherwise it would try it.
So, i had to enable client side TLS and disabling NTLM. It says untrusted connection in the logs, and i tried modifying the mynetworks variable below but couldn't fix it. It may be untrusted because of the invalid exchange certificate. For reference, here is the the main.cf i used. I am aware of the obsolete and unneeded entries. smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache myhostname = helpdesk.seguroscatatumbo.com relayhost = [mar-exch01.seguroscatatumbo.com] smtp_sasl_tls_security_options = smtp_sasl_mechanism_filter = login !ntlm smtp_use_tls = yes smtp_tls_loglevel = 1 smtp_tls_note_starttls_offer = yes smtp_tls_security_level = may smtp_tls_session_cache_timeout = 3600s smtp_tls_CAfile = smtp_sasl_auth_enable = yes smtp_sasl_password_maps = hash:/etc/postfix/sasl/sasl_passwd broken_sasl_auth_clients = yes smtp_always_send_ehlo = yes ### mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128 192.168.100.0/24 /etc/aliases contains one modification: root: myuser /etc/postfix/generic has one line: r...@helpdesk.ourdomain.com myu...@ourdomain.com /etc/postfix/sasl/sasl_passwd has one line: [exchangeserver.ourdomain.com] DOMAIN\myuser:mypass Now, a final question that isn't exactly relevant to postfix. Can i make emails sent to come as "myu...@ourdomain.com" instead of the default "myu...@helpdesk.ourdomain.com" I am aware that my linux box is called "helpdesk" and that /etc/hosts says: 127.0.0.1 helpdesk 127.0.0.1 helpdesk.ourdomain.com helpdesk I tried setting the mydestination in main.cf to ourdomain.com but then postfix didn't try relay to exchange which i guess it's the right behaviour. I am aware that when i configure the helpdesk i may try just impersonating the account as helpd...@ourdomain.com without touching anything else. -- View this message in context: http://postfix.1071664.n5.nabble.com/Exchange-2007-gives-535-5-7-3-Authentication-unsuccessful-tp65072p65126.html Sent from the Postfix Users mailing list archive at Nabble.com.