Installing Certbot on Debian 8 - OS Package Manager Not Installing Certbot

Hi @iggs0

If this is not the issue let us know

There are a couple of other ways of installing certbot

https://certbot.eff.org/docs/install.html#alternate-installation-methods

Certbot-Auto

The certbot-auto wrapper script installs Certbot, obtaining some dependencies from your web server OS and putting others in a python virtual environment. You can download and run it as follows:

user@webserver:~$ wget https://dl.eff.org/certbot-auto
user@webserver:~$ chmod a+x ./certbot-auto
user@webserver:~$ ./certbot-auto --help

Andrei