From cataclysmic recessions to unprecedented climate disasters, our cities seem awash with unintended consequences borne of complex times. While city administrations grapple with developing systemic supports, our infrastructure, communities and individual wellbeing are increasingly succumbing to the strain. This paper examines a practice gaining recent traction for improving our cities’ sustainable resilience: service design. As an inherently user-centered, reflexive and iterative practice, it develops service systems by drawing upon a range of disciplinary roles - from makers to strategists, and ethnographers to technologists. I examine three New York City-based case studies which each attempt to improve the services its residents use and need. While responding to the complex needs of the same city, these case studies illustrate the vastly different possibilities for improving broken civic services through institutional intervention: housing in civic service design, mobility in private sector service design, and online access, in what I term ‘generative’, community-based service design.