Sam Varshavchik, thanks for the help!

Sending encrypted mail is now working through ATT Uverse with stunnel with 
courier. My esmtpauthinfo file was missing the port as parameter.

At:
http://www.courier-mta.org/courier.html

Documentation does not show the ,port or /SECURITY= options when looking at:
esmtpauthclient
This configuration file configures ESMTP authentication for the ESMTP client. 
This is a text file of zero or more lines that contain the following fields:
relay userid password

The description of esmtproutes is described more explicitly:
esmtproutes
This file is used by the ESMTP module, and it contains one or more lines in the 
following form:
domain:relay[,port][/SECURITY=STARTTLS][/SECURITY=NONE]

More info and setup on FreeBSD 9.0:

telnet smtp.att.yahoo.com 587
Trying 98.138.31.74...
Connected to smtp1.sbc.mail.am0.yahoodns.net.
Escape character is '^]'.
220 smtp101.sbc.mail.ne1.yahoo.com ESMTP
ehlo localhost
250-smtp101.sbc.mail.ne1.yahoo.com
250-AUTH LOGIN PLAIN XYMCOOKIE
250-PIPELINING
250-SIZE 41697280
250 8BITMIME
quit


== Courier Send Mail Through ISP ==
cd /usr/local/etc/courier/

# ATTUverse Auth Working (Unencrypted?)
vi esmtpauthclient
 smtp.att.yahoo.com,587 u...@sbcglobal.net PASSWORD
vi esmtproutes
 :smtp.att.yahoo.com,587

# ATTUverse Auth Working (Encrypted through stunnel)
esmtpauthclient
 LOCALHOST.EXAMPLE.COM,2525 u...@sbcglobal.net PASSWORD
esmtproutes
 :LOCALHOST.EXAMPLE.COM,2525

== Stunnel Conf ==
vi /etc/rc.conf
 stunnel_enable="YES"
cd /usr/local/etc/rc.d/
vi stunnel
 : ${stunnel_enable="YES"}
 : ${stunnel_config="/usr/local/etc/stunnel/${name}.conf"}
 : ${stunnel_pidfile="/var/run/stunnel/${name}.pid"}
cd /usr/local/etc/stunnel
cp stunnel.conf-sample stunnel.conf
vi stunnel.conf
 chroot = /var/run/stunnel
 setuid = stunnel
 setgid = stunnel
 pid = /stunnel.pid
 options = NO_SSLv2
 [attsmtp]
 client = yes
 verify = 0
 accept = 2525
 connect = smtp.att.yahoo.com:465
 delay = yes
cd /var/run
mkdir stunnel
chown stunnel:stunnel stunnel
service stunnel start
telnet localhost 2525
ehlo localhost

== Make Stunnel LISTEN on 2525 on restart (Requires Stunnel 4.53) ==
Run the default supfile and update all ports (took me like 30 min):
 csup -g -L 2 -h cvsup5.us.FreeBSD.org /usr/share/examples/cvsup/ports-supfile
pkgtools was used for upgrading:
 portsdb -Fu
 portupgrade stunnel


On 07/20/2012 02:01 PM, John Vasko wrote:
The misplaced colon was a typo in my email. The configuration files are as they should be on the server, and outgoing email still isn't working. I hope that didn't ruin my chances in getting help with my issue.

I tried some variations of esmtproutes (and corresponding changes in esmtpauthclient when trying with gmail) but I get the same "authentication required" error. See Below:

esmtproutes
 :smtp.att.yahoo.com,587
 >> mail gets bounced with auth required

 :smtp.att.yahoo.com,587/SECURITY=STARTTLS
 >> mail gets bounced with unable to set minimum security

 :smtp.att.yahoo.com,465/SECURITY=SSL3
>> mail gets stuck in mailq (SSL3 was just a guess and probably an invalid option)

 :smtp.gmail.com,587
 >> mail gets bounced with auth required

UNDELIVERABLE MAIL
Your message to the following recipients cannot be delivered:
<j...@example.com>:
    gmail-smtp-msa.l.google.com [173.194.79.109]:
>>> MAIL FROM:<j...@vaskos.com> BODY=7BIT SIZE=795
<<< 530-5.5.1 Authentication Required. Learn more at
<<< 530 5.5.1 http://support.google.com/mail/bin/answer.py?answer=14257 jv6sm4551948pbc.40

Please advise.

More Info:

The original document that helped me get emails working on my other non-courier machine was:
http://qiaoyang.blogspot.com/2007/08/sendmail-auth-ssl-tunnel-att-yahoo.html
With the exception that I had the following authinfo:
|AuthInfo: "U:root" "I:j...@sbcglobal.net" "P:xxxxxx" "M:LOGIN PLAIN"|
Instead of:
|AuthInfo: "U:myn...@sbcglobal.net" "I:myn...@sbcglobal.net" "P:xxxxxx" "M:LOGIN PLAIN"|

On 07/20/2012 04:13 AM, Sam Varshavchik wrote:
John Vasko writes:

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

That should be

:smtp.att.yahoo.com,587

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

And that should be

smtp.att.yahoo.com j...@sbcglobal.net PASSWORD


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