SSMTP send off

If you are unlucky enough to work in a corporate environment where they don't trust your Linux machine to send mail, you probably need to relay to some fucked up Exchange server like http://www.themessagecenter.com/ provide. Poor you.

Since SSMTP sucks, since:

I spent a morning migrating from /etc/ssmtp/ssmtp.conf to ~/.msmtprc. The reason why it took so long as msmtp's "auth on" didn't work and after a LOT of debugging, I found the solution to be auth login.

So this is my ~/.msmtprc:

logfile ~/.msmtp.log
auth login
from kai.hendry@example.com
host mail.securembox.com
user kai.hendry@example.com
password secret

My old /etc/ssmtp/ssmtp.conf

hendry@deb02:~$ grep -v "^#" /etc/ssmtp/ssmtp.conf  | grep .
root=hendry
mailhub=mail.securembox.com
AuthUser=kai.hendry@example.com
AuthPass=secret
hostname=deb02.jil.org
FromLineOverride=Yes

You can tell you have authorisation problem with your relay if your spits out like "550 5.7.1 Unable to relay".

Jan 31 10:49:22 host=mail.securembox.com tls=off auth=off from=kai.hendry@example.com recipients=kai.hendry@foo.org smtpstatus=550 smtpmsg='550 5.7.1 Unable to relay' errormsg='recipient address kai.hendry@foo.org not accepted by the server' exitcode=EX_DATAERR

The "auth=off" should be a dead giveaway.

Debug tips

With thanks from https://wiki.archlinux.org/index.php/MSMTP.

Test mail:

$ cat test.mail
To: kai.hendry@foo.org
From: kai.hendry@example.com
Subject: A test

Yadda, yadda, yadda

SSMTP debugging:

cat test.mail | /usr/sbin/ssmtp -d5 kai.hendry@foo.org

the MSMTP log to compare to:

cat test.mail | msmtp -d  kai.hendry@foo.org
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