Grasslands are one of the most imperiled ecosystems in the world and the majority of the grassland ecosystem in the United States is privately owned and used for agriculture. Conversion of grasslands to row crops is expanding, fueled by commodity price increases, technological improvements, and agricultural policy. The U.S. government primarily uses voluntary incentive-based conservation programs to address the environmental impacts of agriculture and encourage conservation on private land. To investigate the utility of these programs to conserve grasslands, we surveyed private landowners in the Plains and Prairie Pothole Ecoregion (PPPE), one of America’s most at-risk grassland areas, about their land use, environmental attitudes and values, and reasons for or against participating in a Farm Bill conservation program. Agricultural landowners with large land holdings, who value hunting, and have positive environmental values, attitudes, and behaviors, were more likely to participate in a program. Financial considerations and a desire for autonomy limited participation. While program participants had less land in grass than nonparticipants and were more likely to convert planted grass to row crops and/or remove wetlands, they were also less likely to convert virgin sod to row crops. These findings signal the need for additional research and tools other than FBCPs to conserve the PPPE grasslands.