In the past several decades, North and South Dakota have experienced increased agricultural expansion and crop rotation simplification, namely an increase in corn (Zea mays L.)– soybean [Glycine max (L.) Merr.] systems. This review investigates the nature and extent of those changes, the underlying causes, and the consequences they have on ecosystem services. The framework of ecosystem services is underutilized in agricultural research, but it can be used to describe the sustainability, resistance, and resilience of the system in relation to these land use changes. The current trends are focused on maximizing provisioning services (i.e., food and fuel) at the expense of regulating, cultural, and supporting services. The decline of regulating services can be seen in increased peak river flow (up to 100% and 200% increases in South and North Dakota, respectively), as well as by the 100% increase in area treated by chemicals, partially due to diminished bioregulation of pests and weeds. The effects on supporting services are demonstrated by altered C balances and water cycling, while the loss of cultural connection to the land is evidenced by a 40% decrease in land conservation since 1997. Overall, these changes are making the land in North and South Dakota more susceptible to stressors, such as drought, crop pests, or even economic trends that could greatly harm these agroecosystems and have nationwide ramifications. To address these changes, producers need to provide a balance of agroecosystem services by optimizing currently available management strategies and possibly transforming agricultural practices for long‐term system stability.