Urban Resilience is the capacity of individuals, communities, institutions, businesses, and systems within a city to survive, adapt, and grow no matter what kinds of chronic stresses and acute shocks they experience. This study looks at the role that infrastructure development and planning can play in ensuring that cities are resilient and adaptable to the uncertain climatic, demographic and socio-economic futures that will unfold. The concept of adaptation tipping points and adaptation pathways is applied to a case study in Singapore for the planning of longterm urban drainage infrastructure. Scenarios developed in this study cover a range of climatic and land-use futures. To study the impact of land use changes 3 scenarios, namely: Current, Green and Sustainable Grey were developed. To understand and justify if the flexibility imparted was worth its cost, economic assessments were performed. This is a valuable extension of the existing framework as it helped to identify the preferred configuration of land use and phase adaptation actions. This understanding is beneficial to decision makers, as it helps in establishing an approximate time scale for adaptation giving time to outline and implement relevant policies.