Worldwide, voluntary agri-environmental programs encourage farmers to adopt environmentally friendly practices. However, the impact of program design on farmers’ participation and long-term practice persistence is unclear. Toward improving program effectiveness, this study illustrates the value of a tailored practice-specific approach to agri-environmental program design. We present a case study of programs promoting cover crops, a conservation practice that can improve soil health and reduce nutrient pollution, drawing from five focus groups with farmers (n = 20) and program administrators (n = 14) in the U.S. Midwest (Iowa, Illinois, and Indiana). Participants perceived cover crop programs to best support farmers is characterized by flexibility and minimal transaction costs. Participants suggested a more data-driven approach to program design particularly for understanding the farm-level economic implications of cover crop use. Integrating financial planning and participatory research components alongside traditional financial incentives and technical assistance were proposed as valuable strategies to enhance program design and broaden the appeal of conservation practices like cover crops.