Urban water management (UWM) is a complex task with a number of constraints especially in developing cities. Rapid population growth, inadequate water infrastructure, and inefficiency in water management policies have led to increased pressure on the city’s water supply and drainage systems. These challenges, however, remain uncertain in terms of both temporal scale and magnitude of change, such as climate change and sea level rise. A city needs an appropriate framework to support not only short-term adaptation activities but also long-term strategies to enhance its resilience to these uncertainties. Therefore, system dynamics—methodologies to frame, understand, and discuss complex issues and problems—is a suitable approach for such complex UWM issues. The purpose of this chapter is to share our experiences in applying a system dynamics approach in Can Tho City, Vietnam. The study went through several steps that involved identifying key stakeholders and tools to support decision making, recognizing exogenous uncertainties and potential measures with their effectiveness indicators, building models to support decision making in present and future scenarios related to the UWM, and engaging stakeholders during the study approach to ensure the complex model results were well taken up and used for their future decisions. Throughout the case study, the system dynamics approach shows its capacity in supporting the city’s policy makers and managers in dealing with such interdisciplinary and complex issues.