Despite recent improvements in overall soil health gained through conservation agriculture, which has become a global priority in agricultural systems, soil and water-related extalities (e.g., wind and water erosion) continue to persist or worsen. Using an inductive, systems approach, we tested the hypothesis that such extalities persist due to expansion of cultivation onto areas unsuitable for sustained production. To test this hypothesis, a variety of data sources and analyses were used to uncover the land and water resource dynamics underlying noteworthy cases of soil erosion (either wind or water) and hydrological effects (e.g., flooding, shifting hydrographs) throughout the central United States. Given the evidence, we failed to reject the hypothesis that cultivation expansion is contributing to increased soil and water extalities, since significant increases in cultivation on soils with severe erosion limitations were observed everywhere the extalities were documented. We discuss the case study results in terms of land use incentives (e.g., policy, economic, and biophysical), developing concepts of soil security, and ways to utilize case studies such as those presented to better communicate the value of soil and water resource conservation. Incorporating the tenets of soil potential and soil risk into soil health evaluations and cultivation decision-making is needed to better match the soil resource with land use and help avoid more extreme soil and water-related extalities.