On FreeBSD 9.0 trying to send mail from courier's cone I get bounced messages 
with:
UNDELIVERABLE MAIL
Your message to the following recipients cannot be delivered:
<u...@gmail.com>:
     smtp1.sbc.mail.am0.yahoodns.net [67.195.15.66]:
>>> MAIL FROM:<j...@example.com> BODY=7BIT SIZE=795
<<< 530 authentication required - for help go to 
http://help.yahoo.com/sbc/dsl/mail/pop/pop-11.html

My relevant configuration is below.

Please advise.

-------------

/usr/local/etc/courier/esmtproutes
  smtp.att.yahoo.com,587

/usr/local/etc/courier/esmtpauthclient
  :smtp.att.yahoo.com j...@sbcglobal.net PASSWORD

/var/log/maillog
  Jul 19 23:27:55 sam courierd: newmsg,id=0002EDE1.5008FA6B.00000C93: dns; 
EXAMPLE.COM (localhost [127.0.0.1])
  Jul 19 23:27:55 sam courierd: 
started,id=0002EDE1.5008FA6B.00000C93,from=<j...@example.com>,module=esmtp,host=gmail.com,addr=<u...@gmail.com>
  Jul 19 23:27:55 sam courierd: Waiting.  shutdown time=none, wakeup time=none, 
queuedelivering=1, inprogress=1
  Jul 19 23:27:56 sam courieresmtp: 
id=0002EDE1.5008FA6B.00000C93,from=<j...@example.com>,addr=<u...@gmail.com>: 
530 authentication required - for help go to 
http://help.yahoo.com/sbc/dsl/mail/pop/pop-11.html
  Jul 19 23:27:56 sam courieresmtp: 
id=0002EDE1.5008FA6B.00000C93,from=<j...@example.com>,addr=<u...@gmail.com>,status:
 failure

  Jul 19 23:27:56 sam courierd: completed,id=0002EDE1.5008FA6B.00000C93
  Jul 19 23:27:56 sam courierd: 
started,id=0002EDE1.5008FA6B.00000C93,from=<>,module=dsn,host=,addr=<j...@example.com>
  Jul 19 23:27:56 sam courierd: Waiting.  shutdown time=none, wakeup time=none, 
queuedelivering=1, inprogress=1
  Jul 19 23:27:56 sam courierd: newmsg,id=0002F503.5008FA6C.00000C97: dns; 
localhost (localhost [127.0.0.1])
  Jul 19 23:27:56 sam courierd: 
started,id=0002F503.5008FA6C.00000C97,from=<>,module=local,host=john!!1001!1001!/www/person/john!!,addr=<john>
  Jul 19 23:27:56 sam courierd: Waiting.  shutdown time=none, wakeup time=none, 
queuedelivering=2, inprogress=2
  Jul 19 23:27:56 sam courierd: completed,id=0002EDE1.5008FA6B.00000C93
  Jul 19 23:27:56 sam courierd: Waiting.  shutdown time=none, wakeup time=none, 
queuedelivering=1, inprogress=1
  Jul 19 23:27:56 sam courierlocal: 
id=0002F503.5008FA6C.00000C97,from=<>,addr=<j...@example.com>,size=2856,success:
 Message delivered.
  Jul 19 23:27:56 sam courierd: completed,id=0002F503.5008FA6C.00000C97
  Jul 19 23:27:56 sam courierd: Waiting.  shutdown time=Fri Jul 20 00:24:09 
2012, wakeup time=Fri Jul 20 00:24:09 2012, queue delivering=0, inprogress=0

------------

Additional Info:

On a different machine, sendmail (not courier sendmail) is able to use a 
smarthost with stunnel to send mail through the same ISP with all the same 
authentication info and validated email address of j...@example.com

However, on the problematic machine, using stunnel with courier gives the same 
"530 authentication required" in the logs and bounced mail. See relevant 
stunnel config below:

/usr/local/etc/stunnel/stunnel.conf
  [attsmtp]
  client = yes
  verify = 0
  accept = 127.0.0.1:2525
  connect = smtp.att.yahoo.com:465
  delay = yes


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