Tropical forests continue to be plagued by the dual sustainability challenges of deforestation and rural poverty. We seek to understand why many of the farmers living in the Brazilian Amazon, home to the world’s largest tropical agricultural-forest frontier, persist in agricultural activities associated with low incomes and high environmental damage. To answer this question, we assess the factors that shape the development and distribution of agricultural activities and farmer well-being in these frontiers. Our study utilizes a uniquely comprehensive social-ecological dataset from two regions in the eastern Brazilian Amazon and employs a novel conceptual framework that highlights the interdependencies between household attributes, agricultural activities, and well-being. We find that livestock production, which yields the lowest per hectare incomes, remains the most prevalent land use in remote areas, but many examples of high income fruit, horticulture, and staple crop production exist on small properties, particularly in peri-urban areas. The transition to more profitable land uses is limited by lagging supply chain infrastructure, social preferences, and the fact that income associated with land use activities is not a primary source of perceived life quality. Instead subjective well-being is more heavily influenced by the nonmonetary attributes of a rural lifestyle (safety, tranquility, community relations, etc.). We conclude that transitions away from low-income land uses in agricultural-forest frontiers of the Brazilian Amazon need not abandon a land-focused vision of development, but will require policies and programs that identify and discriminate households based on a broader set of household assets, cultural attributes, and aspirations than are traditionally applied. At a broader scale, access to distant markets for high value crops must be improved via investments in processing, storage, and marketing infrastructure.