Sustainable, conservation-oriented agricultural practices like shade coffee and agroforestry can enhance conservation objectives in tropical landscapes. Adoption of these practices, however, is influenced by numerous factors. We conducted a survey of 89 coffee farmers in Puerto Rico to understand their farming practices, experience with existing incentives, and willingness to participate in conservation programs. Quantitative analysis showed that current farming practices, farm size, and annual income from farming were associated with willingness to participate in conservation programs. Qualitative results suggested that financial considerations, conflicting state and federal incentives, lack of information about conservation programs, distrust in government, and land use restrictions might hinder participation. Some farmers perceived that sun farming—a practice incompatible with sustainable conservation—was required to be eligible for state agricultural incentives. The way some farmers practiced shade farming differed from the way suggested for conservation purposes, particularly in the type of shade trees and their cover density. Farmers highlighted the need for financial incentives to encourage adoption of shade farming. They also expressed concerns that participation in conservation programs could limit their land management autonomy. We suggest that availability of financial incentives, reconciliation of institutional barriers, increased outreach, and involvement of farmers in design of conservation programs can increase adoption and retention of conservation practices.