Sstrhsrtj

sender_email - email address that does not exist, but must be used as FROM address, because receiver host rejects emails from other emails.

receiver_email - email that is supposed to receive the sent message

local_smtp - SMTP server that is installed on another computer in the local network and forwards all received messages to external_smtp

external_smtp - SMTP server that is installed on a computer in another network and rejects all emails that do not come from sender_email

I have configured sendmail to send emails from sender_email and authenticate with user/password to local_smtp that is supposed to send the email message further to external_smtp that only accepts emails sent from a specific email, which is sender_email in this case. However, judging from the log files sendmail authenticates with external_smtp instead of local_smtp. I do not want to authenticate with external_smtp, because that is up to local_smtp.

logfile:

10745 <<< Subject: Terminal Email Send

10745 <<<

10745 <<< Email Content line 1

10745 <<< Email Content line 2

10745 <<< [EOF]

10759 === CONNECT local_smtp.

10759 <<< 220 **********************************************************************^M

10759 >>> EHLO mgmt-snmp

10759 <<< 250-local_smtp says hello^M

10759 <<< 250-AUTH LOGIN PLAIN^M

10759 <<< 250-VRFY^M

10759 <<< 250 8BITMIME^M

10759 >>> MAIL From:<sender_email> AUTH=sender_email

10759 <<< 530 authentication required^M

10759 >>> This is a MIME-encapsulated message

10759 >>>

10759 >>> --t8IEdmbX010759.1442587188/mgmt-snmp

10759 >>>

10759 >>> The original message was received at Fri, 18 Sep 2015 16:39:48 +0200

10759 >>> from root@localhost

10759 >>>

10759 >>>    ----- The following addresses had permanent fatal errors -----

10759 >>> receiver_email

10759 >>>     (reason: 530 authentication required)

10759 >>>

I guess it has something to do with AUTH=sender_email, but I do not know how to change it.

sendmail.mc:

divert(-1)dnl

#-----------------------------------------------------------------------------

# $Sendmail: debproto.mc,v 8.14.4 2014-02-11 13:02:08 cowboy Exp $

#

# Copyright (c) 1998-2010 Richard Nelson.  All Rights Reserved.

#

# cf/debian/sendmail.mc.  Generated from sendmail.mc.in by configure.

#

# sendmail.mc prototype config file for building Sendmail 8.14.4

#

# Note: the .in file supports 8.7.6 - 9.0.0, but the generated

#   file is customized to the version noted above.

#

# This file is used to configure Sendmail for use with Debian systems.

#

# If you modify this file, you will have to regenerate /etc/mail/sendmail.cf

# by running this file through the m4 preprocessor via one of the following:

#   * make   (or make -C /etc/mail)

#   * sendmailconfig 

#   * m4 /etc/mail/sendmail.mc > /etc/mail/sendmail.cf

# The first two options are preferred as they will also update other files

# that depend upon the contents of this file.

#

# The best documentation for this .mc file is:

# /usr/share/doc/sendmail-doc/cf.README.gz

#

#-----------------------------------------------------------------------------

divert(0)dnl

#

#   Copyright (c) 1998-2005 Richard Nelson.  All Rights Reserved.

#

#  This file is used to configure Sendmail for use with Debian systems.

#

define(`_USE_ETC_MAIL_')dnl

include(`/usr/share/sendmail/cf/m4/cf.m4')dnl

VERSIONID(`$Id: sendmail.mc, v 8.14.4-4.1ubuntu1 2014-02-11 13:02:08 cowboy Exp $')

OSTYPE(`debian')dnl

DOMAIN(`debian-mta')dnl

dnl # Items controlled by /etc/mail/sendmail.conf - DO NOT TOUCH HERE

undefine(`confHOST_STATUS_DIRECTORY')dnl        #DAEMON_HOSTSTATS=

dnl # Items controlled by /etc/mail/sendmail.conf - DO NOT TOUCH HERE

dnl #

dnl # General defines

dnl #

dnl # SAFE_FILE_ENV: [undefined] If set, sendmail will do a chroot()

dnl #   into this directory before writing files.

dnl #   If *all* your user accounts are under /home then use that

dnl #   instead - it will prevent any writes outside of /home !

dnl #   define(`confSAFE_FILE_ENV',             `')dnl

dnl #

dnl # Daemon options - restrict to servicing LOCALHOST ONLY !!!

dnl # Remove `, Addr=' clauses to receive from any interface

dnl # If you want to support IPv6, switch the commented/uncommentd lines

dnl #

FEATURE(`no_default_msa')dnl

dnl DAEMON_OPTIONS(`Family=inet6, Name=MTA-v6, Port=smtp, Addr=::1')dnl

DAEMON_OPTIONS(`Family=inet,  Name=MTA-v4, Port=smtp')dnl

dnl DAEMON_OPTIONS(`Family=inet6, Name=MSP-v6, Port=submission, M=Ea, Addr=::1')dnl

DAEMON_OPTIONS(`Family=inet,  Name=MSP-v4, Port=submission, M=Ea, Addr=127.0.0.1')dnl

dnl #

dnl # Be somewhat anal in what we allow

define(`confPRIVACY_FLAGS',dnl

`needmailhelo,needexpnhelo,needvrfyhelo,restrictqrun,restrictexpand,nobodyreturn,authwarnings')dnl

dnl #

dnl # Define connection throttling and window length

define(`confCONNECTION_RATE_THROTTLE', `15')dnl

define(`confCONNECTION_RATE_WINDOW_SIZE',`10m')dnl

dnl #

dnl # Features

dnl #

dnl # use /etc/mail/local-host-names

FEATURE(`use_cw_file')dnl

dnl #

dnl # The access db is the basis for most of sendmail's checking

FEATURE(`access_db', , `skip')dnl

dnl #

dnl # The greet_pause feature stops some automail bots - but check the

dnl # provided access db for details on excluding localhosts...

FEATURE(`greet_pause', `1000')dnl 1 seconds

dnl #

dnl # Delay_checks allows sender<->recipient checking

FEATURE(`delay_checks', `friend', `n')dnl

dnl #

dnl # If we get too many bad recipients, slow things down...

define(`confBAD_RCPT_THROTTLE',`3')dnl

dnl #

dnl # Stop connections that overflow our concurrent and time connection rates

FEATURE(`conncontrol', `nodelay', `terminate')dnl

FEATURE(`ratecontrol', `nodelay', `terminate')dnl

dnl #

dnl # If you're on a dialup link, you should enable this - so sendmail

dnl # will not bring up the link (it will queue mail for later)

dnl define(`confCON_EXPENSIVE',`True')dnl

dnl #

dnl # Dialup/LAN connection overrides

dnl #

include(`/etc/mail/m4/dialup.m4')dnl

include(`/etc/mail/m4/provider.m4')dnl



dnl LOCAL_CONFIG

dnl EXPOSED_USER(root uucp)dnl # users exempt from masquerading

dnl LOCAL_USER(root)dnl

dnl MASQUERADE_AS(`external_smtp')dnl

dnl FEATURE(`allmasquerade')dnl

dnl FEATURE(`masquerade_envelope')dnl

dnl FEATURE(`nullclient', local_smtp)dnl



LOCAL_CONFIG

## Custom configurations below (will be preserved)

define(`SMART_HOST', `local_smtp')dnl

define(`confAUTH_MECHANISMS', `EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl

FEATURE(`authinfo', `hash /etc/mail/authinfo')dnl

define(`RELAY_MAILER_ARGS', `TCP $h 25')dnl

dnl #

dnl # Default Mailer setup

MAILER_DEFINITIONS

MAILER(`local')dnl

MAILER(`smtp')dnl

authinfo:

AuthInfo:local_smtp "U:root" "I:my_username" "P:my_password"

As root send a test message with tracking map (authinfo) lookups.

#!/bin/sh

# -d60.5 turn on traking map lookups

/usr/sbin/sendmail -d60.5 -v -i -fsender_email -- receiver_email  <<END

subject: test



test

END

Possible outcomes to define next tests:

• no authinfo lookups


• authinfo lookups with keys other than you expected


• authinfo lookups returning "no match"


• authinfo lookups returning correct values