<p>Cover cropping is an effective management practice for reducing nitrogen (N) losses to the environment from agriculture fields in the Midwest. Cereal rye (CR; <i>Secale cereale L</i>.) and hairy vetch (HV; <i>Vicia villosa Roth</i>) are two of the most common cover crop species grown in the region. However, limited cover crop adoption in the region is partly due to a dearth of knowledge addressing the effect of cover crops on nitrogen cycling and grain production within corn and soybean conservation cropping systems. The following studies were designed to address knowledge gaps in the current literature regarding the rate, quantity, and timing of cover crop residue C and N release; the fate of CR N following termination; and the effects of cover crops specifically on soybean growth, N assimilation, and yield. Data from this study revealed that growers should be aware that cover crop nutrient release may result in a “tug-of-war” between the soil microbiome and cash crops for soil inorganic-N. Additionally, we observed that CR N is used minimally by the subsequent crop; thus, growers should value CR N as a long-term benefit, such as building SOM. Finally, we found that added pressure from CR during early soybean growth may reduce soybean resilience, and in a wet year result in yield loss.</p>