Successful conservation strategies have increasingly looked beyond bounded protected areas and toward integrated landscape approaches that conserve biodiversity while maintaining ecosystem services that benefit human communities and food production. More integrated approaches to conservation are particularly timely in agricultural landscapes, where individual farm-level choices can play a significant role in the management of habitat provisioning, nutrient cycling, recreation amenities, carbon sequestration, and the delivery of clean water. This study presents results of an interdisciplinary analysis with shade coffee farmers in the Pico Duarte region of the Dominican Republic. Findings suggest that small farms, as part of a diversified livelihood strategy, maintain a diverse tree canopy, which supports soil conservation and important watershed services. However, high poverty levels and strong economic pressures to convert to high-input, monoculture crops are threatening native tree species biodiversity and the provisioning of ecosystem services (e.g., delivery of clean water and carbon sequestration) to local beneficiaries, as well as to national and international actors. A coordinated effort to support smallholder shade coffee farmers across the landscape through agricultural extension, capacity building, and other market-and-non-market-based interventions offer the potential to improve rural livelihoods and ecosystem services conservation over the long-term.