In the U.S. Corn Belt states of Illinois, Iowa, and Indiana, 94% of crop production is dedicated to corn and soybeans. Agricultural diversification — encompassing a broader range of crops, livestock, and non-crop species — offers potential benefits for farm resilience, local food systems, rural community vitality, and ecological outcomes. However, structural and institutional barriers impede this transition, requiring policy-level intervention. This paper presents findings from the Reimagining Agricultural Diversity (RAD) initiative, a three-year participatory research process involving farmers and agricultural stakeholders across the region. Through iterative collaborative meetings, participants identified key challenges to diversification and co-developed a set of ranked policy opportunities evaluated on feasibility and transformative potential. Four priority areas emerged: (1) federal crop insurance reform under Farm Bill Title XI to better accommodate diversified production systems; (2) improvements to conservation incentive programs under Title II, including EQIP, CRP, and CSP, to more directly incentivize production diversity; (3) investment in post-harvest market infrastructure — including storage, aggregation, processing, and manufacturing — for diversified agricultural products; and (4) expansion of institutional procurement frameworks to build durable local markets. Findings are intended to inform policymakers and agricultural decision makers seeking to foster more resilient and regenerative food systems in the Corn Belt.