This chapter discusses the implications of automation on everyday urban living. It takes the example of automatic cleaning machines at Singapore’s Changi Airport to think more broadly about the potential of robots in reshaping the everyday lives and livelihoods of workers, users and managers in the city. In particular, robots are not simply poised to change the nature of urban jobs and replace some vocations by becoming faster and more efficient than humans. They also have the capacity to influence perceptions, expectations and reactions of citizens and urban managers alike. Focusing on the encroachment of automation on everyday spaces and tasks, the chapter raises urgent and critical questions around the politics of lives and livelihoods. It also draws attention to the risks of deferring urban experiences and responsibilities to algorithmic calculations and rationalities.