Question : Outgoing email fails with FreeBSD on ATT UVERSE

Recently my ISP was switched to ATT UVERSE from the original SBC Yahoo DSL and I am having difficulty getting outgoing emails working from my webserver.  Incoming emails seem to work fine as well as a HTTP hosting/SSH/etc...  Everything worked perfectly before the switch...

Basically my setup is same as here:
http://rajasuperman.blogspot.com/2006/09/gmail-as-smarthost-for-fre_115764792412436946.html

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But ONLY things I really changed was smtp.sbcglobal.net to smtp.att.yahoo.com

1. Edited 1 line in /etc/mail/auth/client-info
AuthInfo:smtp.att.yahoo.com "U:root" "I:[email protected]" "P:PASSWORD"

2. Edited 1 line in /etc/mail/freebsd.mc
define(`SMART_HOST',`smtp.att.yahoo.com')dnl

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From /var/log/maillog

Jan  1 17:36:21 blue sm-mta[55047]: n020Qou3054631: to=, ctladdr= (1008/1008), delay=01:09:31, xdelay=00:01:15, mailer=relay, pri=300530, relay=smtp.att.yahoo.com [69.147.64.31], dsn=4.0.0, stat=Defe
rred: Operation timed out with smtp.att.yahoo.com

Jan  1 18:00:38 blue sendmail[55177]: STARTTLS=client, relay=[127.0.0.1], version=TLSv1/SSLv3, verify=FAIL, cipher=DHE-RSA-AES256-SHA, bits=256/256

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How do I get my outgoing emails working again?  What do I need to do?

Answer : Outgoing email fails with FreeBSD on ATT UVERSE

Looks like Outgoing SMTP mail works with stunnel now on FreeBSD...

From /var/log/messages
Jan  5 12:30:39 blue stunnel: LOG5[93914:134791168]: attsmtp accepted connection from 127.0.0.1:50315
Jan  5 12:30:40 blue stunnel: LOG5[93914:134791168]: attsmtp connected remote server from 192.168.X.XX:49408
Jan  5 12:30:40 blue stunnel: LOG5[93914:134791168]: CRL: verification passed
Jan  5 12:30:40 blue stunnel: LOG5[93914:134791168]: VERIFY OK: depth=0, /C=US/ST=California/L=Santa Clara/O=Yahoo! Inc./OU=Yahoo/CN=smtp.att.yahoo.com
Jan  5 12:30:40 blue stunnel: LOG5[93914:134791168]: CRL: verification passed

from /var/log/maillog
Jan  5 12:24:53 blue sm-mta[99057]: n055qvuG095777: to=, ctladdr= (1008/1008), delay=14:31:56, xdelay=00:00:00, mailer=relay, pri=3360530, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (ok 1231187335 qp 40759)

The solution was actually posted at:
http://qiaoyang.blogspot.com/2007/08/sendmail-auth-ssl-tunnel-att-yahoo.html

Some useful info missing is this link is that instead of editing the relay port directly in /etc/mail/sendmail.cf you can add the following line in /etc/mail/my.site.com.mc:
define(`RELAY_MAILER_ARGS', `TCP $h 2525')

Also from the link... I would still like to know what to write in /etc/mail/my.site.com.mc so I don't actually have to comment out the sendmail.cf file that reads:
R< $=w > $* $@ $2 delete local host

Another thing that was misleading from the link is that you can't make comments with:
! #

You should just use:
#

Also, my auth info for relay used root at the username. ie):
AuthInfo: "U:root" "I:[email protected]" "P:xxxxxx" "M:LOGIN PLAIN"

Also, because I had to edit the sendmail.cf file directly... From [/etc/mail] I had to do:
1. make all install restart
2. manually edit sendmail.cf to comment out the line mentioned above.
3. make restart

Aside from this last part the stunnel configuration was very confusing... I created folders and changed directories from the default configuration... ie) It does NOT work out of the box. Here are some of the commands I used to help configure:

/usr/local/etc/rc.d/stunnel restart
vi /var/log/messages
vi /usr/local/etc/stunnel/stunnel.conf
vi /usr/local/etc/rc.d/stunnel
vi /etc/rc.conf
ps aux |grep stunnel
netstat -na |grep LIST

And in stunnel.conf
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[attsmtp]
client = yes
verify = 0
accept = 127.0.0.1:2525
connect = smtp.att.yahoo.com:465
delay = yes