Anticipatory thinking is a critical component in urban planning practices and knowledge systems in an era of unpredictability and conflicting expectations of the future. This chapter introduces “anticipatory resilience” as a futures-oriented knowledge system that intentionally addresses uncertain climate conditions and explores alternative, desirable future states. It suggests a portfolio of tools suitable for building long-term foresight capacity in urban planning. Examples of knowledge systems interventions are presented to explore the trade-offs, constraints, possibilities, and desires of diverse future scenarios co-generated in settings with people that hold different perspectives, knowledge, and expectations.