If diversified farming systems (DFS) are to thrive again in the United States, policies and preferences must evolve to reward the environmental and social benefits of sustainable farming and landscape management. Compared with conventional agricultural policies, policies aiding ecological diversification are underdeveloped and fragmented. We consider several examples of obstacles to the adoption and spread of diversified farming practices in the U.S. industrialized agricultural system. These include the broader political economic context of industrialized agriculture, the erosion of farmer knowledge and capacity, and supply chain and marketing conditions that limit the ability of farmers to adopt sustainable practices. To overcome these obstacles and nurture DFS, policy makers, researchers, industry, farmers, consumers, and local communities can play pivotal roles to transform agricultural research, develop peer-to-peer learning processes, support the recruitment and retention of new farmers through access to credit and land, invest in improved agricultural conservation programs, provide compensation for provision of ecological services in working landscapes, and develop links to consumer and institutional markets.