The water sector is, currently and for the foreseeable future, challenged by rising levels of uncertainty in demand and availability of water, in a context of aging infrastructure and limited investment. In order to support strategic planning, water companies need a way to assess how their system behaves when faced with a range of changing conditions (climatic trends, asset deterioration, behavioral patterns, etc.) as well as accidents/incidents and/or extreme events (wildcards). In this study, a resilience assessment methodology was demonstrated, with 'stress tests' alternative water system configurations (including systems designed with decentralized or distributed philosophies) under a range of scenarios and extreme events. A 'resilience profile graph' was developed to quantify the performance of each configuration. The methodology was applied to the real-world urban water system of Oasen, which supplies the eastern part of the Province of South Holland, where the current system configuration and two potential future configurations were tested (one decentralized and one distributed). We show how the concept of resilience, operationalized through this methodology, can assist long term decision making and support strategic infrastructure planning.