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Much of São Paulo’s urban expansion is driven by the development of informal settlements on its periphery, which includes the catchment areas that provide important environmental services such as open space and catchments for drinking water reservoirs. In such areas, governance of land, water services and water resources, traditionally administered separately, are in fact interdependent. A role-playing game was built to explore the interactions between different actors (mayor, water company, district representatives and landowners of different types) in land tenure insecurity, water and sanitation infrastructure and pollution in the periphery of São Paulo. An assessment of the game sessions revealed the different points of view of local and institutional actors about the main issues and the possible negotiation arrangements. Institutional actors misunderstood the hierarchy and diversity of community actors’ preoccupations, which were related more to land tenure, access to public transport and other aspects such as health and education rather than to water and sanitation infrastructure. Institutional actors also failed to recognize how access to infrastructure and land tenure is shaped by power-based relationships. While community actors appreciated the game and felt that they had learned from the experiment, institutional actors were more critical. These discrepancies call into question the potential effectiveness of the legal, technical and institutional solutions that the institutional actors are promoting to address the pollution issue.