When installing letsencrypt use the installer packages from letsencrypt. The Ubuntu packages can be a bit dated and result in buggy issues that have been resolved.
Use the Certbot PPA For those of you who may already have installed the old libraries you can do the following to uninstall and install the new libraries.
First, install the new repositories.
sudo add-apt-repository ppa:certbot/certbot sudo apt-get update
Then remove your old libraries.
sudo apt remove certbot python3-certbot
Finally, install the new libraries. Since I usually use NGINX as my web server this line adds the NGINX component. But you can also install the apache 'python3-certbot-apache' file as well.
sudo apt-get install certbot python3-certbot letsencrypt python3-certbot-nginx python-certbot-doc