Unattended Upgrades on Ubuntu

Create the new VM and ssh into it

$ mkdir myUnattendedUpgradesDemoVM
$ cd myUnattendedUpgradesDemoVM
$ vagrant init ubuntu/xenial64
$ vagrant up
$ vagrant ssh

Install and enable unattended upgrade

unattended-upgrade isn’t enabled by default (even after you apt install it), so you have to run dpkg-reconfigure to enable it:

$ sudo apt install unattended-upgrades
$ sudo dpkg-reconfigure unattended-upgrades

Answer yes to Automatically download and install stable updates?

Accept the default origins pattern, which configures unattended-upgrade to install only stable and security upgrades.

Test it

First do a dry-run:

$ sudo unattended-upgrade -v -d --dry-run

If everything looks good, do a real run:

$ sudo unattended-upgrade -v -d

Email notifications

To get unattended-upgrade to send you email notifications you need to install a program that provides the mailx command (the command that unattended-upgrade calls when it wants to send an email) and a Mail Transfer Agent (MTA) program (a program that actually sends the emails, that the mailx command talks to), and make sure that the root user can send mails using the mailx command.

I want an MTA that’s able to use the SMTP server of my email provider (Gmail, FastMail etc) so that it can send emails to my real email account (rather than doing something like appending to files in /var/spool/mail/).

msmtp is an MTA with SMTP support that’s easy to set up.

Install mstmp:
```
$ sudo apt install msmtp msmtp-mta bsd-mailx
```
bsd-mailx is a package that provides an msmtp-compatible mailx command, and msmtp-mta hooks mstmp up to the mailx command.

Create an msmtp config file for the root user:

$ sudo nano /root/.msmtprc

Here’s an example of what the contents of this file should look like for FastMail:

account        fastmail
host           smtp.fastmail.com
port           465
from           <YOU>@<YOUR_DOMAIN>
user           <YOU>@fastmail.com
password       <A_FASTMAIL_APP_PASSWORD_FOR_SMTP>
auth           on
tls            on
tls_starttls   off
tls_certcheck  off
logfile        /root/.msmtp.log
account default : fastmail

Test that the root user can successfully send email using the mailx command:

echo "This is the email body" > /tmp/body.txt && sudo mailx -s "This is the subject" YOU@YOUR_DOMAIN < /tmp/body.txt; rm /tmp/body.txt

Tell unattended-upgrade what email address to send emails to. Edit /etc/apt/apt.conf.d/50unattended-upgrades and set the Unattended-Upgrade::Mail setting:
```
Unattended-Upgrade::Mail "<YOU>@<YOUR_DOMAIN>"
```

Logging

Email notifications are better, but it’s worth knowing that unattended-upgrade logs everything in the /var/log/unattended-upgrades/ directory. /var/log/unattended-upgrades/unattended-upgrades.log contains recent log entries. Older log entries are in the log dir in gzip files. And there’s also a /var/log/unattended-upgrades/unattended-upgrades-shutdown.log file.

Reboots

TODO: What’s the default behaviour when a reboot is required? Send an email?

You can set Unattended-Upgrade::Automatic-Reboot in /etc/apt/apt.conf.d/50unattended-upgrades to reboot automatically.

There’s also a reboot-notifier package but it seems to conflict with a bunch of Ubuntu and Gnome desktop packages.

New releases

TODO: How do you get it to email you or do the upgrade when a new release upgrade is available?

Hypothesis’s servers have a /etc/cron.weekly/update-notifier-common script containing [ -x /usr/lib/ubuntu-releaseupgrader/release-upgrade-motd ] || exit 0 that does this, comes from the update-notifier-common package which is a dependency of update-notifier, but this seems to be installed by default. Is it enabled to send email notifications by default?