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I'm trying to setup sendmail on FreeBSD to relay (outbound) through an Exchange server on the MSA port via SMTP-AUTH. The Exchange server is already successfully relaying for Java applications that connect and do SMTP-AUTH via MSA directly. However, applications which rely on sendmail are getting <<< 550 5.7.1 Unable to relay errors. Here's my current (excluding comments) .mc:

divert(0)
VERSIONID(`$FreeBSD: release/9.2.0/etc/sendmail/freebsd.mc 249867 2013-04-25 01:46:20Z gshapiro $')
OSTYPE(freebsd6)
DOMAIN(generic)   
FEATURE(access_db, `hash -o -T<TMPF> /etc/mail/access')
FEATURE(blacklist_recipients)
FEATURE(local_lmtp)
FEATURE(mailertable, `hash -o /etc/mail/mailertable')
FEATURE(virtusertable, `hash -o /etc/mail/virtusertable')
FEATURE(authinfo,`hash -o /etc/mail/auth/client-info')
define(`SMART_HOST', `mail.ourdomain.com')
define(`confCW_FILE', `-o /etc/mail/local-host-names')
DAEMON_OPTIONS(`Name=IPv4, Family=inet')
DAEMON_OPTIONS(`Name=IPv6, Family=inet6, Modifiers=O')
define(`confBIND_OPTS', `WorkAroundBrokenAAAA')
define(`confNO_RCPT_ACTION', `add-to-undisclosed')
define(`confPRIVACY_FLAGS', `authwarnings,noexpn,novrfy')
MAILER(local)
MAILER(smtp)
define(`RELAY_MAILER_ARGS', `TCP $h 587')
define(`confAUTH_MECHANISMS', `EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')

auth/client-info (hashed into a db) has:

AuthInfo:mail.ourdomain.com: "U:relay@ourdomain.com" "P:password"

edit

The nightly log e-mailed out a new error with my latest config Warning: Option: AuthMechanisms requires SASL support (-DSASL) Looks like I need to recompile sendmail to add SASL support now.

edit

I installed the ports version of sendmail (with SASL support), and pointed the mailer config at it. I no longer receive SASL warnings, but am still unable to relay mail.

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    Try to see what's going on, stop sendmail and run /usr/sbin/sendmail -bD -X /tmp/test.log, then tail -f /tmp/test.log and try again – Sergio Apr 9 '15 at 17:31

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