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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 ...
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  1. #1
    Just Joined!
    Join Date
    Sep 2007
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    7

    Sendmail problems - outgoing mail


    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?

  2. #2
    Just Joined!
    Join Date
    Sep 2007
    Posts
    7
    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?

  3. #3
    Just Joined!
    Join Date
    Sep 2007
    Posts
    7
    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.

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