Telling sendmail to auth?

i had the same issue. Finally made it with several configurations.

/etc/mail/sendmail.mc
    define('SMART_HOST','smtp.yourdomain.com')dnl
    define('confAUTH_OPTIONS','A')dnl
    FEATURE('authinfo','hash -o /etc/mail/authinfo.db')dnl
    MASQUERADE_AS('yourdomain.com')dnl
    FEATURE(masquerade_envelope)dnl
    FEATURE(masquerade_entire_domain)dnl
    MASQUERADE_DOMAIN('yourdomain.com.')dnl
    FEATURE('relay_based_on_MX')dnl
    FEATURE('genericstable')dnl
    GENERICS_DOMAIN('localhost.localdomain')dnl

/etc/mail/authinfo (660 permissions)
    Authinfo:yourdomain.com "U:yoursmtpuserid" "P:yourpassword" "M:PLAIN"
    Authinfo: "U:yoursmtpuserid" "P:yourpassword" "M:PLAIN"

>makemap hash /etc/mail/authinfo < /etc/mail/authinfo

/etc/mail/access (660 permissions)
    connect:localhost.localdomain RELAY
    connect:localhost RELAY
    connect:127.0.0.1 RELAY

>makemap hash /etc/mail/access < /etc/mail/access


/etc/genericstable
    root [email protected]

>makemap hash /etc/mail/genericstable < /etc/mail/genericstable


/etc/named.conf
    options{
          listen-on port 53 {127.0.0.1;};
    };

>cp -f /etc/named.conf /var/named/chroot/etc/

/etc/resolve.conf
    nameserver  127.0.0.1
    nameserver  youriplocal
    domain      localdomain

>chkconfig -> named on
          -> saslauthd on
          -> sendmail on

>service named restart
>service saslauthd restart
>service sendmail restart

To test it you can execute:

sendmail -Am -t -v to:emaildestination from:youremail

I hope it works for you.

My short configuration in sendmail.mc for SMTP Auth as a client for mailjet.com :

include(`/etc/mail/sasl/sasl.m4')dnl
define(`SMART_HOST', `[in-v3.mailjet.com]')dnl
define(`RELAY_MAILER_ARGS', `TCP $h 587')dnl

587 because port 25 is blocked. STARTTLS and ESMTP are now automaticely in Sendmail. Before, libsasl2-modules (in addition to the not necessary libsasl2-modules-db) and sasl2-bin must be installed. Thinks to switch to START=yes in /etc/defa ult/saslauthd (in debian)

In access:

AuthInfo:mailjet.com "U:5xxxxx" "P:f6xxxxxx" "M:LOGIN PLAIN DIGEST-MD5 CRAM-MD5"

And finally, run /usr/share/sendmail/update_auth.

So, there are only 2 files to modify sendmail.mc and access. After of course, make in /etc/mail then service sendmail restart.

ps: A lot of tutorial, add :587 after AuthInfo:mailjet.com, it's AMHA an error. A debug -d60.5 (different lookup map) it's my prove.

For sendmail, I usually manage SMTP auth by adding an entry in /etc/mail/access. A quick example for your setup is here:

# /etc/mail/access
# by default we allow relaying from localhost...
localhost.localdomain           RELAY
localhost                       RELAY
127.0.0.1                       RELAY
AuthInfo:in.mailjet.com "U:smmsp" "I:myusername" "P:mypassword" "M:PLAIN"

Save that and restart the sendmail daemon, /sbin/service sendmail restart.

Did you run:

makemap hash client-info < client-info

Unless you build the client-info.db file from the text one using the command above, the information that is in there, is not read by sendmail

EDIT #1:

From the bat book I copy that:

When sendmail connects to another host, and that other host offers to authenticate, that connected-to host’s IP address, hostname, and domain are looked up in the database.

If the IP address, host, or domain is not found, the connection is allowed, but sendmail will not attempt to authenticate it. Otherwise, the information in the matching right column is returned for sendmail to use.

You are connecting to in6.mailjet.com which is an MX for in.mailjet.com. So maybe you have to change your AuthInfo: line to:

AuthInfo:mailjet.com "U:myusername" "P:mypassword" "M:PLAIN"

EDIT #2:

You seem to have a minor typo in the FEATURE(authinfo) declaration:

FEATURE(`authinfo', `hash -o /etc/mail/auth/client-info.db')dnl

Remove -o (optional) from feature authinfo and restart/reload sendmail. It will make sendmail refuse to start without access to authinfo map/file.

FEATURE(`authinfo',`hash ...')

Repeat sending you test email with tracking map lookups (includes tracking authinfo map lookups)

sendmail -d60.5 -AM -t -v

Does sendmail look for authinfo entries? [The answear should narrow list of possible problems]