The impacts of fair trade on smallholders are complex, multilayered, and often contradictory. This chapter details why and how geographic, political-economic, and cultural context shapes fair trade’s impacts. Specifically, it explores the impacts of fair trade within different domains, including income and livelihoods, community development, social organization, environment and sustainability, and gender equity. The chapter ends with an assessment of some of the challenges and opportunities shaping fair trade and smallholder participation in the present and in the years to come. Findings suggest that future research should intentionally explore the ways in which fair trade impacts are shaped by local realities will help us identify the most effective practices and policies for improving smallholder livelihoods, organizational capacity, and overall well-being.