In tropical regions, shifting from forests and traditional agroforestry to intensive plantations generates conflicts between human welfare (farmers’ demands and societal needs) and environmental protection. Achieving sustainability in this transformation will inevitably involve trade-offs between multiple ecological and socioeconomic functions. To address these trade-offs, our study used a new methodological approach allowing the identification of transformation scenarios, including theoretical landscape compositions that satisfy multiple ecological functions (i.e., structural complexity, microclimatic conditions, organic carbon in plant biomass, soil organic carbon and nutrient leaching losses), and farmers needs (i.e., labor and input requirements, total income to land, and return to land and labor) while accounting for the uncertain provision of these functions and having an actual potential for adoption by farmers. We combined a robust, multi-objective optimization approach with an iterative search algorithm allowing the identification of ecological and socioeconomic functions that best explain current land-use decisions. The model then optimized the theoretical land-use composition that satisfied multiple ecological and socioeconomic functions. Between these ends, we simulated transformation scenarios reflecting the transition from current land-use composition towards a normative multifunctional optimum. These transformation scenarios involve increasing the number of optimized socioeconomic or ecological functions, leading to higher functional richness (i.e., number of functions). We applied this method to smallholder farms in the Jambi Province, Indonesia, where traditional rubber agroforestry, rubber plantations, and oil palm plantations are the main land-use systems. Given the currently practiced land-use systems, our study revealed short-term returns to land as the principal factor in explaining current land-use decisions. Fostering an alternative composition that satisfies additional socioeconomic functions would require minor changes (“low-hanging fruits”). However, satisfying even a single ecological indicator (e.g., reduction of nutrient leaching losses) would demand substantial changes in the current land-use composition (“moonshot”). This would inevitably lead to a profit decline, underscoring the need for incentives if the societal goal is to establish multifunctional agricultural landscapes. With many oil palm plantations nearing the end of their production cycles in the Jambi province, there is a unique window of opportunity to transform agricultural landscapes.