Cover crops are known to promote many aspects of soil and water quality, yet estimates find that in 2012 only 2.3% of the total agricultural lands in the Midwestern USA were using cover crops. Focus groups were conducted across the Corn Belt state of Iowa to better understand how farmers confront barriers to cover crop adoption in highly intensive agricultural production systems. Although much prior research has focused on analyzing factors that help predict cover crop use on farms, there is limited research on how farmers navigate and overcome field-level (e.g. proper planting of a cover crop) and structural barriers (e.g. market forces) associated with the use of cover crops. The results from the analysis of these conversations suggest that there is a complex dialectical relationship between farmers’ individual management decisions and the broader agricultural context in the region that constrains their decisions. Farmers in these focus groups shared how they navigate complex management decisions within a generally homogenized agricultural and economic landscape that makes cover crop integration challenging. Many who joined the focus groups have found ways to overcome barriers and successfully integrate cover crops into their cropping systems. This is illustrated through farmers’ descriptions of their ‘whole system’ approach to cover crops management, where they described how they prioritize the success of their cover crops by focusing on multiple aspects of management, including changes they have made to nutrient application and modifications to equipment. These producers also engage with farmer networks to gain strategies for overcoming management challenges associated with cover crops. Although many participants had successfully planted cover crops, they tended to believe that greater economic incentives and/or more diverse crop and livestock markets would be needed to spur more widespread adoption of the practice. Our results further illustrate how structural and field-level barriers constrain individual actions, as it is not simply the basic agronomic considerations (such as seeding and terminating cover crops) that pose a challenge to their use, but also the broader economic and market drivers that exist in agriculturally intensive systems. Our study provides evidence that reducing structural barriers to adoption may be necessary to increase the use of this conservation practice to reduce environmental impacts associated with intensive agricultural production.