This paper lays out the relationships between three mutually reinforcing concepts associated with agroecosystems: (1) agroecosystem health, the extent to which an agroecosystem can meet human needs for all of its residents over time; (2) resilience, the capacity of a system to adapt, reorganize, and maintain key functions in the face of turbulent and unpredictable change in its environment; (3) food security, sufficient quantity and quality of food for everyone at all times. Agroecosystem health has been defined by a number of properties including the following: stability, sustainability, equitability, productivity, and autonomy, each in the context of specific spatial and temporal scales. Indicators that characterize biophysical and social conditions including soil health, biodiversity, topography, farm economics, land economics, and social organization can be combined using analytical hierarchy process to map agroecosystem health across a landscape. The resulting map may provide incentive and guidance for improving the conditions underlying agroecosystem health. Resilience and agroecosystem health overlap largely because both rely on diversity, in biological and physical as well as human cultural, social, and economic terms. The Agroecosystems Management Program at The Ohio State University has approached research and outreach to improve agroecosystem health, resilience, and food security by encouraging self-organizing social networks for economic development around local and regional agricultural supply chains, encouraging farm enterprise diversity at a wider range of farming scales, and conducting research to monitor and estimate the benefits of such diversification. Social media tools have been explored for connecting entrepreneurs at the planning stage, with the ultimate goal of improving the economic support for more diversified enterprises in agroecosystems. Although challenging, such adaptive management experiments may create and encourage new opportunities for managing agroecosystem health, and with it, resilient food production and security.