The US government is in the process of requiring secure connections to its public web services through HTTPS and HSTS. It is a lot of hard work by a lot of good people working in an enterprise of enterprises of enterprises, and it is not strongly centrally coordinated. This talk will discuss the technical and political challenges that have come up during the process, offer a glimpse into the US government's evolving relationship with technology, and share some lessons that may be useful to those pushing for change in their own bureaucracies.