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Date:      Sun, 28 Jun 2015 20:36:58 +0000 (UTC)
From:      Christian Weisgerber <naddy@mips.inka.de>
To:        freebsd-questions@freebsd.org
Subject:   Sendmail: SMTP auth and smart host?
Message-ID:  <slrnmp0mna.rg3.naddy@lorvorc.mips.inka.de>

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I'm trying to add a very standard piece of configuration to my sendmail
setup: Send all mail to a smart host and use SMTP client authentication
for talking to the smart host.

There are many examples, howtos, tutorials, etc. about this all over the
net, e.g.
https://www.dnsexit.com/support/mailrelay/sendmail.html

Define the smart host, set the authentication information in the
access database, and sendmail will automagically use it for SMTP
AUTH.

Alas, the magic doesn't happen:

------------------------------------------------------------------------
naddy@unix-ag.uni-kl.de... Connecting to [127.0.0.1] via relay...
220 lorvorc.mips.inka.de ESMTP Sendmail 8.14.9/8.14.9; Sun, 28 Jun 2015 22:01:07 +0200 (CEST)
>>> EHLO lorvorc.mips.inka.de
250-lorvorc.mips.inka.de Hello localhost [127.0.0.1], pleased to meet you
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-EXPN
250-VERB
250-8BITMIME
250-SIZE
250-DSN
250-ETRN
250-DELIVERBY
250 HELP
>>> VERB
250 2.0.0 Verbose mode
>>> MAIL From:<naddy@lorvorc.mips.inka.de> SIZE=27
250 2.1.0 <naddy@lorvorc.mips.inka.de>... Sender ok
>>> RCPT To:<naddy@unix-ag.uni-kl.de>
>>> DATA
250 2.1.5 <naddy@unix-ag.uni-kl.de>... Recipient ok
354 Enter mail, end with "." on a line by itself
>>> .
050 <naddy@unix-ag.uni-kl.de>... Connecting to mail.inka.de. via relay...
050 220 mail.inka.de ESMTP Exim - mail ready at Sun, 28 Jun 2015 22:01:07 +0200
050 >>> EHLO lorvorc.mips.inka.de
050 250-mail.inka.de Hello dslb-188-104-157-230.188.104.pools.vodafone-ip.de [188.104.157.230]
050 250-SIZE 67108864
050 250-8BITMIME
050 250-PIPELINING
050 250-STARTTLS
050 250 HELP
050 >>> STARTTLS
050 220 TLS go ahead
050 >>> EHLO lorvorc.mips.inka.de
050 250-mail.inka.de Hello dslb-188-104-157-230.188.104.pools.vodafone-ip.de [188.104.157.230]
050 250-SIZE 67108864
050 250-8BITMIME
050 250-PIPELINING
050 250-AUTH PLAIN LOGIN
050 250 HELP
050 >>> MAIL From:<naddy@mips.inka.de> SIZE=382
050 250 OK
050 >>> RCPT To:<naddy@unix-ag.uni-kl.de>
050 >>> DATA
050 550 relay not permitted
050 503-All RCPT commands were rejected with this error:
050 503-relay not permitted
050 503 Valid RCPT command must precede DATA
050 >>> RSET
050 250 Reset OK
050 <naddy@lorvorc.mips.inka.de>... Connecting to local...
050 <naddy@lorvorc.mips.inka.de>... Sent
250 2.0.0 t5SK17H8027901 Message accepted for delivery
naddy@unix-ag.uni-kl.de... Sent (t5SK17H8027901 Message accepted for delivery)
Closing connection to [127.0.0.1]
>>> QUIT
221 2.0.0 lorvorc.mips.inka.de closing connection
------------------------------------------------------------------------

As the -v output shows, sendmail simply never attempts to use client
authentication.  _Something_ must be wrong or missing, but I don't
see it.

sendmail.mc:
------------------------------------------------------------------------
OSTYPE(freebsd6)
MASQUERADE_AS(`mips.inka.de')
FEATURE(accept_unresolvable_domains)
FEATURE(access_db)
FEATURE(allmasquerade)
FEATURE(masquerade_envelope)
FEATURE(local_procmail)
FEATURE(use_cw_file)
define(`ALIAS_FILE', `/etc/mail/aliases,-o /etc/mail/aliases.newsgate')
define(`LUSER_RELAY', `local:dev-null')
define(`SMART_HOST', `[mail.inka.de]')
define(`UUCP_MAILER_MAX', 0)
DAEMON_OPTIONS(`Name=IPv4, Family=inet')
DAEMON_OPTIONS(`Name=IPv6, Family=inet6')
MAILER(local)
MAILER(smtp)
MAILER(../../../../local/share/sendmail/bsmtp)
MAILER(uucp)
------------------------------------------------------------------------

access database:
------------------------------------------------------------------------
AuthInfo:mail.inka.de "U:xxxx" "I:xxxx" "P:yyyy" "M:PLAIN"
------------------------------------------------------------------------


(Meanwhile I'm sending this by UUCP... because it works.)
-- 
Christian "naddy" Weisgerber                          naddy@mips.inka.de



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