America’s remaining grassland in the Prairie Pothole Region (PPR) is at risk of being lost to crop production. When crop prices are high, like the historically high corn prices that the U.S. experienced between 2008 and 2014, the risk of grassland conversion is even higher. Changing climate will add uncertainties to any efforts toward conservation of grassland in the PPR. Grassland conversion to cropland in the region would imperil nesting waterfowl among other species and further impair water quality in the Mississippi watershed. In this project, we sought to contribute to the understanding of land conversion in the PPR with the aim to better target the use of public and private funds allocated toward incentivizing grassland preservation on private lands in the Dakotas. We assembled data on historical land switching in the area and on land conversion costs. We analyzed crop vulnerabilities to weather and climate change. We examined practical analytical tools to assess the likelihood of grassland conversion to cropping. With our weather-yield-land use modeling framework we evaluated the likely outcomes of land use changes in the region. Among other land use patterns, our research indicated a possible increase of grassland acres as grasses could be less adversely impacted by changing climate. Working with farmers and conservation partners, our project assessed drivers of land use changes. In particular, while economics and climate factors were admittedly obvious important motivations for land use changes, our findings suggested that landowners’ decisions were significantly affected by non-pecuniary factors, like lifestyle choices, or some behavioral biases (e.g., recency bias, and anticipated regret factor) whose roles in economic decision making have been increasingly recognized. As landowners and conservation managers gradually adapt to changing climates, it is not only important that we understand the impacts of the changing climates, but also imperative that we are aware how landowners perceive how climate is changing and how well they are willing to embrace sound adaptation strategies.