Urban areas around the world are facing increased challenges in consistently and reliably providing water services. Rapid urbanization, climate change, and the disjointed management of water distribution systems reveal the need for the creation of holistic management solutions. San Francisco Public Utilities Commission (SFPUC) is considering alternative water supply options to improve the reliability of San Francisco’s water resource, which provided a case study for this research. This research proposes an alternative planning tool used for systematic urban water supply planning and demand management. This approach compares water supply options using the Water Evaluation and Planning tool (WEAP) and a drought resilience matrix. Future implications of modeled climate change, extreme drought, and population increase effects on the natural and urban water system are explored in this study. The effectiveness of water supply portfolios is compared through the creation and use of a drought resilience matrix.