earthlink has decided to shut off smtp.earthlink.net port 25
which I had working fine using:
define(`SMART_HOST',`smtp.earthlink.net')dnl

I noticed this with Thunderbird and changed configuration to
smtpauth.earthlink.net port 587 and Thunderbird works fine.
telnet smtpauth.earthlink.net 587
works fine

sendmail on the other hand when trying to send an email, thru squirrelmail writes to /var/log/maillog

Nov 11 17:57:35 www sendmail[8156]: nABNkN1H007776: to=<user@edu.edu>, ctladdr=<user@www.mydomain.org> (500/500), delay=00:11:12, xdelay=00:00:00, mailer=relay, pri=390721, relay=smtpauth.earthlink.net. [207.69.189.202], dsn=4.0.0, stat=Deferred: smtpauth.earthlink.net.: No route to host



I changed my /etc/mail/sendmail.mc to modify/add:
define(`SMART_HOST',`smtpauth.earthlink.net')dnl
define(`confLOG_LEVEL',`40')dnl
TRUST_AUTH_MECH(`LOGIN PLAIN')dnl
define(`confAUTH_MECHANISMS', `LOGIN PLAIN')dnl
FEATURE(`authinfo',`hash /etc/mail/auth/client-info')dnl

and create the file /etc/mail/auth/client-info as
AuthInfo:smtpauth.earthlink.net:587 "U:user@earthlink.net" "I:user@earthlink.net" "Password" "M:PLAIN LOGIN"

and run the commands
makemap hash client-info < client-info
chmod 600 client-info*
service sendmail restart

but the same message is logged to /var/log/maillog
with the added confLOG_LEVEL message I get the additional messages
Nov 11 17:57:35 www sendmail[8156]: nABNkN1H007776: makeconnection (smtpauth.earthlink.net. [207.69.189.201]) failed: No route to host

I change /etc/mail/auth/client-info and rerun the commands to have a
bogus smtp server address and there is no change in the output to
/var/log/maillog, i.e. I do not think the authinfo is doing anything.

How to debug ???

Hi,

Port 587 is the submission port and has nothing to do with authinfo.
Anyway you can read this post and use the smarthost-submit.mc as suggested at the end.

Regards

Thanks for the information.
I seem to be one step closer, but not there yet, to having it working but I am more confused.

The sendmail configuration line:
define(`RELAY_MAILER_ARGS', `TCP $h 587')dnl

eliminates the 'No route to host' problem.
Now the emails sent through squirrelmail are bounced back by
my(?) sendmail indicating that authentication was supposed to take place
but did not:
The original message was received at Fri, 13 Nov 2009 15:15:13 -0600
from user.mydomain.org [127.0.0.1]

----- The following addresses had permanent fatal errors -----
<user@edu.edu>
(reason: 550 Please configure your mail client to use authentication.)

----- Transcript of session follows -----
... while talking to smtpauth.earthlink.net.:
>>> DATA
<<< 550 Please configure your mail client to use authentication.
550 5.1.1 <user@edu.edu>... User unknown
<<< 503-All RCPT commands were rejected with this error:
<<< 503-Please configure your mail client to use authentication.
<<< 503 Valid RCPT command must precede DATA

Most of the sendmail configuration in smarthost-submit.mc at the
referenced link was already in my sendmail.mc file. The lines
DOMAIN(generic)dnl
FEATURE(`genericstable')
GENERICS_DOMAIN(`myhost')
are not in my sendmail.mc and I have not implemented them, although
I suspect that these lines are not the problem and they are not what
I want.

In your reply you seem to be suggesting that authinfo is not the configuration/feature that is used by sendmail to act as a client
to another MAILER-DAEMON. The web page http://www.sendmail.org/~ca/email/auth.html section "Using sendmail as a client with AUTH" seems to indicate that this is how to tell sendmail
the hostname/login/password of the ISP account that is used in the authentication handshaking. So the question I have is how do I tell sendmail to:
a) do authentication when forwarding mail to smtpauth.earthlink.net
b) the account and password to use to authenticate

Note that I do not want the emails to look like they are comming from
the earthlink account I want the email to look like they are comming
from user@mydomain.org.

Hi,

What I said is that your problem has nothing to do with authinfo, rather than with the fact you have to connect to smarthost's port 587 (that is the submission port). Of course you have to use the AUTH config options in submit.mc

Again, thanks for the information.

It turns out that the last problem was a feeble attempt at
setting the port was left in the authinfo file:
authinfo:smtpauth.earthlink.net:587 "U:user@earthlink.net" "Password"

with the :587 removed sendmail acting as a client to earthlink works fine.

I was surprised that sendmail seems to quietly ignore the fact that
the information was bogus. Is there some way to turn on debugging to
detect this?

You can run sendmail in test mode (-bt) with debugging turned on, or use tcpdump to see what happens during connection.

Regards