While agroforestry is promoted in many regions worldwide, limited attention is paid to farmer-led transitions toward agroforestry. Agroforestry systems (AFS) are ubiquitous and structure the landscapes along the east coast of Madagascar. These systems are managed by smallholders and produce a variety of products, some for export (mainly clove products, vanilla, and lychees), others for self-consumption or for sale locally (including fruit, tubers, timber and fuelwood). We compared information in historical documents with data collected in household surveys in 2016 in one village to identify the socio-technical and economic determinants that guided farmers' strategies over a century and led to the current production systems and landscapes. The agricultural policy implemented by the French colonial power, required farmers to produce industrial crops for export. Reluctantly at first, farmers gradually abandoned shifting rice cultivation (tavy) to grow cash crops, mainly coffee, paving the way for an economy based on trade and monetization. Later, farmers replaced coffee by clove trees, gradually transforming shifting cultivation into AFS with cloves. Simultaneously, they extended paddy rice cultivation and diversified their AFS in response to economic and climatic disturbances and to more gradual changes, thereby demonstrating their continual responsiveness. Similar dynamics can be observed in many contexts where the colonial powers forced farmers to produce cash crops to supply industries in the metropolitan area, obliging them to diversify their production and cropping systems. Our results provide valuable insights into the multiple drivers of these transitions toward agroforestry and into the complexity of the processes involved.