Millions of smallholder farmers face the daunting challenge of sustaining or improving productivity in the face of rising input costs, limited access to input and output markets, climate vagaries, and depleted natural resources. These farmers’ objectives and circumstances are diverse, varying with both their biophysical environments and their socioeconomic and cultural contexts. Agroecological intensification (AEI), or the integration of agroecological principles into farm and system management, can improve the performance of agriculture—“performance” being locally defined and potentially including productivity, nutrition, resilience, and sustainability. In principle, AEI is relevant for all forms of agriculture, whether it is pursued as a business, as a means to support family nutrition, or for both income and self-provisioning. Conventional approaches to research and extension are, however, poorly designed to support AEI across diverse socio-ecological contexts, particularly given the weakness of research and extension systems in food-insecure parts of the world. Because agroecological principles must be implemented in a context-dependent manner and AEI is a knowledge-intensive process, delivering the benefits of AEI requires a radical reconsideration of the ways in which agricultural knowledge is produced and shared. Emerging developments in participatory methods, as well as in information and communications technologies (ICT), can contribute to innovative strategies that allow systematic matching of options—diversification strategies, crops or varieties, agronomic practices, and market arrangements—across heterogeneous contexts.