In this paper, we discuss a challenging water resources problem in a developing world city, Chennai, India. The goal is to reconstruct past system behavior and diagnose the causes of a major water crisis. In order to do this, we develop a hydrologic-engineering-economic model to address the complexity of urban water supply arising from consumers' dependence on multiple interconnected sources of water. We integrate different components of the urban water system: water flowing into the reservoir system; diversion and distribution by the public water utility; groundwater flow in the aquifer beneath the city; supply, demand, and prices in the informal tanker-truck-based water market; and consumer behavior. Both the economic and physical impacts of consumers' dependence on multiple sources of water are quantified. The model is calibrated over the period 2002–2006 using a range of hydrologic and socio-economic data. The model's results highlight the inadequacy of the reservoir system and the buffering role played by the urban aquifer and consumers' coping investments during multiyear droughts.