Everyone knows that there is no privacy in our communications, including email. While we can’t stop that, we can make it harder for them.

MSMTP randomize your outgoing SMTP servers

I don’t run a mail server these days, so I run MSMTP to send outbound mail from my Linux boxes. I don’t want every email that I send out to go to the same smtp server, so I’ve randomized things a bit.

I have a folder with multiple msmtprc files in it “.MSMTPconfigs”.

ls ~/.MSMTPconfigs/
msmtprc.fastmail  msmtprc.gmail  msmtprc.hotmail  msmtprc.secretmail.org

Obiously you need to know how to create some msmtprc files. This is a sample for Gmail:

#sample file

account gmail
host smtp.gmail.com
from your-username@gmail.com
auth on
user username@gmail.com
password SecretPassword
# Use TLS.
tls on
tls_trust_file /etc/ssl/certs/ca-certificates.crt
# Syslog logging with facility LOG_MAIL instead of LOG_USER.
syslog LOG_MAIL
account default: gmail

You’ll want to have a handful of free email servers that you can “relay” through and create msmtprc files for, Gmail, fastmail.fm, hotmail, outlook.com are all good enough!

Then I have a script that runs from cron every 5 minutes or so:

#!/bin/bash
files=(/home/user/.MSMTPconfigs/*)
# Grab a random config file
n=${#files[@]}
SMTP=”${files[RANDOM % n]}”
# make the random config file the .msmtprc
cp $SMTP /home/user/.msmtprc

Filed under: Configs - @ February 23, 2013 8:18 pm

Tags: add-ons, carnivore, echelon, email, email monitoring, extensions, msmtp, smtp, smtpselect, the man, thunderbird