This chapter focuses on one of the largest early computer systems in the world: the British Ministry of Pensions system, which recorded and manipulated data on millions of citizens paying income tax into the welfare state in the 1950s. Citizens who interacted with these machines labored digitally “off the clock” to protect their livelihoods and solidify their identities. From 1950 through 1970, hundreds of transgender Britons tried to hack this system—and hack gender itself. They sought to normalize and legitimize their identities in the eyes of the state, taking aim at the Ministry’s massive computerized systems. This chapter recovers the Ministry’s response, showing how it hid behind the strictures of their computing systems to argue that digital gender changes were not necessary for proper pension payments. Trans citizens took the opposite tack—leveraging the logic of the digital systems that ran the state to re-code their identities, attempting to get computer logic to encode a gender change. Ultimately, this chapter shows that the history of off-the-clock digital labor—done to establish or maintain our identities—has a long, varied history. Knowing this history can help us understand the diversity in our current technosocial networks and how centralized computer infrastructures silently shape our lives.