This study was conducted over 190,000 historical farm‐level dryland row‐crop yield observations (corn, sorghum, soybeans, and winter wheat) spanning over 7000 Kansas farms from 1973 to 2018 coupled with agroclimatic variables to assess the performance of a broad range of weather‐and area‐based insurance products. Results showed substantial levels of basis risk across agroclimatic‐based indices, limited ability to reduce income variability under fair pricing, and underperformance relative to area‐based yield products. Growth‐stage specific heat indices for corn and soybeans may offer an effective risk management tool. Implications in the context of current agricultural policy initiatives and climate change adaptation are discussed.