Let's Encrypt launhced on April 12th 2016, for the first time allowing anyone access to free SSL certificates that could be automatically fetched and renewed. The demand was massive, and so was the need for a client to fetch these certificates for all of those users. This client is called Certbot, and it's written entirely in Python. Unfortunately for the sanity of Certbot developers, these users of Let's Encrypt can't decide on a single operating system to use! This requires us to ship our software, and all of its dependencies, to a variety of systems all with different web servers, Python versions, package managers,and underlying packages. Learn how we got through this mess!