I previously wrote an article around configuring msmtp on Ubuntu 12.04, but as I hinted at in my previous post that sort of got lost when the upgrade of my host to Ubuntu 16.04 went somewhat awry. What follows is essentially the same post, with some slight updates for 16.04. As before, this assumes that you’re using Apache as the web server, but I’m sure it shouldn’t be too different if your web server of choice is something else.

I use msmtp for sending emails from this blog to notify me of comments and upgrades etc. Here I’m going to document how I configured it to send emails via a Google Apps account, although this should also work with a standard Gmail account too.

To begin, we need to install 3 packages:
sudo apt-get install msmtp msmtp-mt ca-certificates
Once these are installed, a default config is required. By default msmtp will look at /etc/msmtprc, so I created that using vim, though any text editor will do the trick. This file looked something like this:

# Set defaults.
# Enable or disable TLS/SSL encryption.
tls on
tls_starttls on
tls_trust_file /etc/ssl/certs/ca-certificates.crt
# Setup WP account's settings.
host smtp.gmail.com
port 587
auth login
password <PASSWORD>
logfile /var/log/msmtp/msmtp.log

account default : <MSMTP_ACCOUNT_NAME>

Any of the uppercase items (i.e. <PASSWORD>) are things that need replacing specific to your configuration. The exception to that is the log file, which can of course be placed wherever you wish to log any msmtp activity/warnings/errors to.

Once that file is saved, we’ll update the permissions on the above configuration file — msmtp won’t run if the permissions on that file are too open — and create the directory for the log file.

sudo mkdir /var/log/msmtp
sudo chown -R www-data:adm /var/log/msmtp
sudo chown 0600 /etc/msmtprc

Next I chose to configure logrotate for the msmtp logs, to make sure that the log files don’t get too large as well as keeping the log directory a little tidier. To do this, we create /etc/logrotate.d/msmtp and configure it with the following file. Note that this is optional, you may choose to not do this, or you may choose to configure the logs differently.

/var/log/msmtp/*.log {
rotate 12

Now that the logging is configured, we need to tell PHP to use msmtp by editing /etc/php/7.0/apache2/php.ini and updating the sendmail path from
sendmail_path =
sendmail_path = "/usr/bin/msmtp -C /etc/msmtprc -a <MSMTP_ACCOUNT_NAME> -t"
Here I did run into an issue where even though I specified the account name it wasn’t sending emails correctly when I tested it. This is why the line account default : <MSMTP_ACCOUNT_NAME> was placed at the end of the msmtp configuration file. To test the configuration, ensure that the PHP file has been saved and run sudo service apache2 restart, then run php -a and execute the following

mail ('personal@email.com', 'Test Subject', 'Test body text');

Any errors that occur at this point will be displayed in the output so should make diagnosing any errors after the test relatively easy. If all is successful, you should now be able to use PHPs sendmail (which at the very least WordPress uses) to send emails from your Ubuntu server using Gmail (or Google Apps).

I make no claims that this is the most secure configuration, so if you come across this and realise it’s grossly insecure or something is drastically wrong please let me know and I’ll update it accordingly.

I’m fairly sure that the title of this post gives away what’s happened, but I’m going to write it down so that I have a small reminder to myself to make sure something like this doesn’t happen again!

It all started when I decided to upgrade my server from Ubuntu 14.04 to the latest LTS release. I did it the normal way using sudo do-release-upgrade but something evidently went wrong; when I rebooted the server everything came back up and online as expected, but everything suddenly stopped working and claimed something about a read-only file system. Being completely unsure what to do, and my linux skills not being what they once were, I had one option… create a new server!

I managed to get it set up fairly quickly and got everything up and running the same night, so that took a little pressure off. I was then given a lesson that I’ve been taught before, but evidently not learned from! I lost the database as a result of the errors, but the last backup I had was from 2014 when I originally switched hosting providers – a rookie mistake, I know – countering that though, is the clear sign that I need to configure regular backups; I’ll be looking at the best ways I can handle that in the coming weeks.

In the meantime, I have 5 or 6 (there’s a chance 2 will be merged) posts to write so I’ll get them written up and posted at a relatively regular interval. The first one up will be to re-do the post I previously had about configuring MSMTP on Ubuntu as that was very regularly viewed according to the site stats.