Question : Sendmail authentication configuration for outgoing mail relay on Solaris

I have downloaded and am attempting to set up a Solaris 10 system to use mail relay for a small number of outgoing emails.  I have an email account and thus a username and password for this provider.

I have set this exact configuration up in the past with different providers but I am running into issues I am unable to resolve.

I compiled and installed sendmail 8.13.8 using the sasl libraries and an appropriate sendmail.mc file

I am attempting to use the /etc/mail/default-auth-info files for holding the authentication data as I have in the past but nothig is working.

Here are some usefull outputs:

RUN FROM LOCAL HOST
sendmail -d0.1 -bv root
Version 8.13.8
 Compiled with: DNSMAP LOG MAP_REGEX MATCHGECOS MILTER MIME7TO8 MIME8TO7
                NAMED_BIND NDBM NETINET NETINET6 NETUNIX NIS NISPLUS PIPELINING
                SASLv2 SCANF XDEBUG

============ SYSTEM IDENTITY (after readcf) ============
      (short domain name) $w = Charon
  (canonical domain name) $j = Charon.localdomain
         (subdomain name) $m = localdomain
              (node name) $k = Charon
========================================================

quit

telnet localhost 80
Trying 127.0.0.1...
Connected to localhost.
Escape character is '^]'.
220 Charon.localdomain ESMTP Sendmail 8.13.8/8.13.8; Wed, 9 Apr 2008 13:22:16 -0600 (MDT)
ehlo localhost
250-Charon.localdomain 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
quit
221 2.0.0 Charon.localdomain closing connection
Connection to localhost closed by foreign host.

END

I am concerned that I did not get an "AUTH" output line from the telnet.  Thus I am not certain that authorization is enabled.

SENDMAIL.MC FILE
divert(0)dnl
VERSIONID(`$Id: ITI-solaris.mc,v 8.13 2001/06/27 21:46:30 gshapiro Exp $')
OSTYPE(solaris2)dnl
DOMAIN(generic)dnl
define(`confFALLBACK_SMARTHOST', `mailhost$?m.$m$.')dnl
MAILER(`local')dnl
MAILER(`smtp')dnl
define(`SMART_HOST', `smtpout.secureserver.net')dnl
define(`confAUTH_MECHANISMS', `EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
define(`confDEF_AUTH_MECHANISMS',`/etc/mail/default-auth-info')dnl
FEATURE(`authinfo',`dbm /etc/mail/default-auth-info')dnl
define(`confAUTH_OPTIONS', `A')dnl
TRUST_AUTH_MECH(`EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl

LOCAL_NET_CONFIG
R$* < @ $* .$m. > $*    $#esmtp $@ $2.$m $: $1 < @ $2.$m. > $3

END OF SENDMAIL.MC FILE


DEFAULT-AUTH-INFO FILE
AuthInfo:smtpout.secureserver.net "U:@.net" "I:@.net" "P:" "M:Plain"

END DEFAULT-AUTH-INFO FILE


When I run mailx from the command line I get the following verbose dialog

[email protected]... Connecting to [127.0.0.1] via relay...
220 Charon.localdomain ESMTP Sendmail 8.13.8/8.13.8; Wed, 9 Apr 2008 13:29:09 -0600 (MDT)
>>> EHLO Charon.localdomain
250-Charon.localdomain 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: SIZE=93
250 2.1.0 ... Sender ok
>>> RCPT To:
>>> DATA
250 2.1.5 ... Recipient ok
354 Enter mail, end with "." on a line by itself
>>> .
050 ... Connecting to smtpout.secureserver.net via relay...
050 220 smtpauth22.prod.mesa1.secureserver.net ESMTP
050 >>> EHLO Charon.localdomain
050 250-smtpauth22.prod.mesa1.secureserver.net
050 250-AUTH LOGIN PLAIN
050 250-8BITMIME
050 250 PIPELINING
050 >>> QUIT
050 221 Good bye.
050 ... Deferred: Temporary AUTH failure
250 2.0.0 m39JT93B005472 Message accepted for delivery
[email protected]... Sent (m39JT93B005472 Message accepted for delivery)
Closing connection to [127.0.0.1]
>>> QUIT
221 2.0.0 Charon.localdomain closing connection


Any and all help is appreciated.

Answer : Sendmail authentication configuration for outgoing mail relay on Solaris

Well, I got it figured out.  The entries into the sendmail.mc file are VERY order specific and must be entered in the correct order or things will not work as expected.