Letsencrypt certbot auto review not working (Debian, Ubuntu) systemd

If your letsencrypt SSL certificates are not renewed automatically, chances are that your certbot.timer service is not running.

Here are the steps to troubleshoot this issue:

1. List all current systemd timers
(see if Certbot is listed, chances are it is not listed)

systemctl list-timers --all

2. Verify that these files exist:

/lib/systemd/system/certbot.service
/lib/systemd/system/certbot.timer
/etc/cron.d/certbot

Note that there is no need to create a separate cron jon to trigger the renawal if these files exist.

3.Start the Certbot Timer
If the files above exist then run the following command to start the timer service

systemctl start certbot.timer

4.Enable the Timer on BOOT
Now enable the timer service on boot

systemctl enable certbot.timer

5.Verify
List all the timers again to verify that certbot is running

systemctl list-timers --all

Unattended Upgrades Ubuntu

First:  Install the unattended upgrade package

sudo apt-get install unattended-upgrades

Edit this file accordingly

vim /etc/apt/apt.conf.d/50unattended-upgrades

Install the Update Notifier

apt-get install update-notifier-common

NOTE:
“If you want the script to automatically reboot when needed, you not only need to set Unattended-Upgrade::Automatic-Reboot "true", but you also need to have the “update-notifier-common” package installed. On minimal installations this is not installed by default and without it the automatic updater will never reboot and will not even tell you that you need to reboot manually if you have email notifications configured!

“The files in /etc/apt/apt.conf.d/ are evaluated in lexicographical order with each file capable of overriding values set in earlier files. This makes it insufficient to view the setting in /etc/apt/apt.conf.d/20auto-upgrades and why it is recommended to use apt-config.”

Resources
https://help.ubuntu.com/community/AutomaticSecurityUpdates
https://www.techrepublic.com/article/how-to-enable-automatic-security-updates-on-centos-7-with-yum-cron/