Organic management systems often use tillage to supplement weed control; however, these practices can harm soil health and function. Reductions in tillage are possible in organic rotations when cover crops are implemented. This thesis evaluated management systems for reductions in tillage in organic corn and soybean systems in two relevant organic cropping regions in the United States, New York and Wisconsin. The first chapter explored two corn-legume living mulch systems and different management strategies to manage weeds and mulch-corn competition. Chapter two investigated yield gaps between cover crop-based organic rotational no-till soybean systems and standard organic full-tillage soybean production with data from 15 site-years of experimental results. Process-based cropping systems models were used to further investigate mechanistic drivers of yield gaps between the two management systems and particularly focus on the effect of dry spring conditions on reduced tillage soybean production in the presence of cereal rye.