Historically, cover crops were valued for reducing soil erosion, providing nitrogen for non-leguminous crops, conserving soil nutrients, and improving soil physical properties. In the last four decades, there has been renewed interest in cover crops as a partial solution to water quality degradation, for building soil health, for making production systems more resilient, and reducing agriculture’s carbon footprint. The wide range cover crop types and potential for providing both on-farm and public benefits creates an equally wide range of factors affecting rates of implementation. Despite the many public benefits provided by cover crops, farmers’ decisions whether to use cover crops tend to focus on the potential for increased profitability. This chapter will consider the factors affecting profitability and approaches to increase cover crop implementation. Lessons learned from a four-decade long effort to increase cover crop use in the Chesapeake Bay watershed to improve water quality will be presented.