Natural resource governance is by nature multi-level, mobilizing various multi-stakeholder arenas in which a social learning approach may play a role. An approach using simulation tools such as role-playing games was tested in metropolitan areas of two South American cities: (1) in the periphery of Cochabamba, to facilitate conflict resolution stemming from the impact of urbanization on the irrigation infrastructure, and (2) in peri-urban areas of S o Paulo, to assist in negotiations on land and water management in a protected catchment. Both interventions were designed to broaden the stakeholders' perspectives and facilitate the exchange of the views of different actors on water and land management using role-playing games. This paper discusses how the scale strategy embedded in the tools and in the mode of participation in fact constrained the possibility of bridging the gap between organisational levels in both situations. This calls for both the crafting of multi-level approaches able to take different levels into account, and finding adequate bridging mechanisms to enhance the integration of learning within organisations and communities.