In the Northwestern uplands of Cambodia, the commodification of agriculture in the 2000 s substituted the traditional rotational and diversified cropping systems with monocropping of commercial crops such as maize and cassava. Driven by high market demand, this transition was associated with deforestation, erosion of soils and biodiversity as well as pollution from increased use of chemical inputs. Land degradation observed after a few years of intensive monocropping undermined the sustainability of the overall agricultural system. However, lessons learned from previous failures of crop boom-bust cycles did not materialize as an incentive to adopt alternative sustainable practices. Along with local villagers we developed a role-play game to investigate farmers' decision-making in relation to land-use transitions and their participation in a Conservation Agriculture (CA) initiative aimed at mitigating land degradation. The game revealed that farmers were still trapped in the boom-bust cycle with commercial crops. Market opportunities and high, short-term economic returns are key parameters in the decision-making process, which mostly overrides environmental aspects. This study shows the importance of opportunity windows for development interventions, the crucial role of farming communities in co-designing alternative cropping systems and the potential of social learning devices to bring CA to scale.