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Abstract Urban water supply systems in the United States are designed to be robust to a wide range of historical hydrological conditions in both their physical infrastructure and in the institutional arrangements that govern their use. However, these systems vary greatly in their capacity to respond to new and evolving stressors on water supplies, such as those associated with climate change. Developing a more precise understanding of the complexity of interactions between the environmental and human components of urban water systems, specifically via their institutions, has the potential to help identify institutional design choices that can foster proactive transitions to more sustainable operating states. This article adapts the Institutional Grammar (IG) within the Robustness of Coupled Infrastructure Systems Framework to assess how a heavily engineered system's institutional configuration may impact its ability to transition to more sustainable management practices. While use of the IG has historically been limited in larger‐N studies, our application demonstrates its flexibility in revealing variation in specific components across cases. The analysis finds the structure of formal institutions shape the interactions between actors differently, and that institutional diversity exists across environmental contexts. The extent to which this institutional diversity drives transitions remains an open question. The results highlight both the importance of and challenges involved with developing longitudinal data on social and natural system interactions.