The highly specialized maize (Zea mays L.) and soybean [Glycine max (L.) Merr.] production system that dominates midwestern U.S. agriculture has led to widespread on-farm and off-farm degradation of and damage to natural resources. The practice of extending maize–soybean rotations with small grains and forages has great potential to balance production and environmental goals, but adoption of these practices is low. Because little is known about farmers’ perspectives on extended rotations, we conducted social survey research with Iowa farmers to address this knowledge gap. Results show that farmers understand the potential benefits of extended rotations using small grains, but they perceive major barriers to use. The highest-rated barriers were structural, such as lack of markets. Structural barriers cannot be easily addressed by individual farmers, indicating that efforts to address negative impacts of specialized commodity production through extended rotations with small grains will require transformative changes in agri-food policies, programs, and ultimately markets.