In 2007 the White House issued a policy instructing all government agencies to enhance their perimeter security by routing connections to the public internet through a Trusted Internet Connection (TIC). Part reverse proxy, part logging system, TICs have been single handedly responsible for some of the greatest scalability challenges facing government IT and have locked billions of dollars in taxpayer money into aging and archaic technology. By 2017 the problem had grown so extreme that the United States Digital Service assembled a team of engineers to figure out how to kill the TIC and move Agencies into the cloud without opening up a wild west of irresponsible security configurations. This is the story of their challenges, complications, own-goals, and engineering factions.