Information is required to understand how novel biodiversity strategies can improve cropping system resilience to climate change. A “business as usual” (BAU) rotation (wheat–canola–wheat–soybean) was compared with a “warm-season crop” (WS) rotation (corn–sunflower–dry bean–canola); a “biodiverse” (BD) rotation (fall rye with cover crop– corn/soybean intercrop—pea/canola intercrop–green fallow mixture); a “perennial grain” (Kernza) rotation (Kernza grain intermediate wheatgrass); and an organic (ORG) rotation (millet-green fallow mixture-wheat). Drought conditions prevailed in both study years. The BAU rotation had the lowest average yield (1821 kg ha⁻¹ compared with 2533 and 3083 kg ha⁻¹ for the BD and WS rotations, respectively), less post-harvest residual biomass, and a lower net return than the WS rotation. The WS rotation was limited by herbicide-resistant weeds in dry beans. Kernza seed yield was five times lower than for spring wheat. ORG wheat yielded the same as other wheat and had a higher net return. Live roots days, a measure of soil health potential, were 95 for the BAU rotation and 174 and 113 for the BD and WS rotations, respectively; the most were recorded for Kernza (365). Seasonal crop growth duration was increased by including Kernza and fall rye for early season growth, and corn, sunflower, a corn–soybean intercrop, a cover crop, and fall-seeded rye for late season growth. WS and BD rotations outperformed the BAU rotation and the BD system accomplished this with half the N fertilizer. Results demonstrate the potential of biodiverse rotations; barriers to their adoption should be addressed.