Sendmail problems - outgoing mail

[w_hairst]

I'm having trouble getting Sendmail configured to work with my Embarq account. I had it working previously, but apparently they changed something. I'm running into a number of problems. Let's start with (probably) the easiest.

Note: These have been edited to remove email addresses, server name, and IP address. For example, google.com would be replaced with (a server).

Trying to send a message in verbose mode, I get the following:
# /usr/lib/sendmail -v (to address) < testmessage
(to address)... Connecting to [127.0.0.1] via relay...
220 (my server) ESMTP Sendmail 8.12.8/8.12.8; Fri, 7 Sep 2007 10:04:23 -0400
>>> EHLO (my server)
250-(my server) Hello localhost.localdomain [127.0.0.1], pleased to meet you
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-8BITMIME
250-SIZE
250-DSN
250-ETRN
250-AUTH LOGIN
250-DELIVERBY
250 HELP
>>> MAIL From:<(originating address)> SIZE=1 AUTH=(originating address)
250 2.1.0 <(originating address)>... Sender ok
>>> RCPT To:<(to address)>
>>> DATA
250 2.1.5 <(to address)>... Recipient ok
354 Enter mail, end with "." on a line by itself
>>> .
250 2.0.0 l87E4Nkl023344 Message accepted for delivery
(to address)... Sent (l87E4Nkl023344 Message accepted for delivery)
Closing connection to [127.0.0.1]
>>> QUIT
221 2.0.0 (my server) closing connection


Trying to send a message from the command line connects to the local machine to send the message, which then connects to Embarq's server? How do I see the transmission to Embarq? Anyway, the message never makes it.

As a temporary workaround (I hope) I put a SMART_HOST line into submit.mc and tried again. Here are the results:

# /usr/lib/sendmail -v (to address) < testmessage
(to address)... Connecting to smtp.embarqmail.com. via relay...
220 mailrelay.embarq.synacor.com ESMTP ecelerity 2.2.0.18 r(18773) Fri, 07 Sep 2007 09:56:41 -0400
>>> EHLO (my server)
250-smtp08.embarq.synacor.com says EHLO to (my IP):21106
250-XDUMPCONTEXT
250-ENHANCEDSTATUSCODES
250-AUTH=LOGIN
250-AUTH LOGIN
250-8BITMIME
250 PIPELINING
>>> AUTH LOGIN =
334 UGFzc3dvcmQ6
>>> *
535 Sorry.
>>> MAIL From:<(originating address)> AUTH=(originating address)
250 MAIL FROM accepted
>>> RCPT To:<(to address)>
>>> DATA
554 Authentication Failed, must login
503 5.5.1 DATA without RCPT TO
>>> RSET
250 RSET OK
root... Connecting to [127.0.0.1] via relay...
220 (my server) ESMTP Sendmail 8.12.8/8.12.8; Fri, 7 Sep 2007 10:10:35 -0400
>>> EHLO (my server)
250-(my server) Hello localhost.localdomain [127.0.0.1], pleased to meet you
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-8BITMIME
250-SIZE
250-DSN
250-ETRN
250-AUTH LOGIN
250-DELIVERBY
250 HELP
>>> MAIL From:<> SIZE=1059
250 2.1.0 <>... Sender ok
>>> RCPT To:<(my server)>
>>> DATA
250 2.1.5 <(my server)>... Recipient ok
354 Enter mail, end with "." on a line by itself
>>> .
250 2.0.0 l87EAZQX023420 Message accepted for delivery
(me)... Sent (l87EAZQX023420 Message accepted for delivery)
Closing connection to [127.0.0.1]
>>> QUIT
221 2.0.0 (my server) closing connection
Closing connection to smtp.embarqmail.com.
>>> QUIT
221 smtp08.embarq.synacor.com closing connection
You have new mail in /var/spool/mail/(me)

Take a good look at the Embarq authentication:
>>> AUTH LOGIN =
334 UGFzc3dvcmQ6
>>> *
535 Sorry.
My server sends AUTH LOGIN =, so Embarq prompts for the password. Yet no login or password are ever sent.

If I connect manually, I get:
# telnet smtp.embarqmail.com 25
Trying 208.47.184.3...
Connected to smtp.embarqmail.com.
Escape character is '^]'.
220 mailrelay.embarq.synacor.com ESMTP ecelerity 2.2.0.18 r(18773) Fri, 07 Sep 2007 10:04:15 -0400
EHLO (my server)
250-smtp08.embarq.synacor.com says EHLO to (my IP):21139
250-PIPELINING
250-ENHANCEDSTATUSCODES
250-AUTH=LOGIN
250-AUTH LOGIN
250-XDUMPCONTEXT
250 8BITMIME
AUTH LOGIN
334 VXNlcm5hbWU6
(my BASE64-encoded username)
334 UGFzc3dvcmQ6
(my BASE64-encoded password)
235 Authed. Go on.
quit
221 smtp08.embarq.synacor.com closing connection
Connection closed by foreign host.

The 'access' file includes:
AuthInfo:mailrelay.embarq.synacor.com "U:(username)" "P:(password)" "M:LOGIN"
AuthInfo:smtp.embarqmail.com "U:(username)" "I:(username)" "P:(password)"
AuthInfo: "U:(username)" "I:(username)" "P:(password)" "M:LOGIN"


Any idea what I'm missing?

[w_hairst]

Upon further examination of the problem:

The key bit here, I think, is the attempted authentication. My Linux box sends "AUTH LOGIN =" when it probably should send "AUTH LOGIN". Connecting via telnet from the Linux machine in question, I can authenticate by sending "AUTH LOGIN", then the username and password, or by sending "AUTH LOGIN (BASE64-encoded username)" and password.

Looks like one of two potential problems:

1: The Linux machine is supposed to send "AUTH LOGIN", but is sending "AUTH LOGIN =" instead, which gets the other server to prompt for the password. Since the username hasn't been sent, the Linux box freaks out and sends a star.

2: The Linux machine can't BASE64-encode the username or password. When it tries to encode the username, the result is =, which gets sent. When it tries to encode the password, the result is *, which gets sent. Since these aren't right, authentication fails.

Is there a way to test the BASE64 encoding portion to ensure proper functionality?

[w_hairst]

Looks like a problem with the older of the two versions. On the existing server, which won't work, I'm running Sendmail 8.12.8. On the replacement server I'm trying to set up, I'm running Sendmail 8.14.1 and it works fine.

Possible problem with "login" authentication on Sendmail 8.12.8? Don't know - but my problems should now be solved.