Winter rye (Secale cereale L.) is a popular cover crop in North Central United States for preventing soil erosion and nutrient losses, among other agronomic and ecosystem benefits. Winter rye can also be a high-quality spring forage option when double-cropped with corn silage (Zea mays L.), thus adding diversity to monocrop rotations. However, these sustainability-promoting benefits have potential trade-offs including soil nutrient immobilization and decreased corn yields. We hypothesized that winter rye would promote sustainable intensification of corn silage, as substantiated by decreased nitrogen budget and soil nitrate without yield loss. We also predicted that winter rye double-cropped and harvested as a forage would maintain total production (corn silage + rye harvest) compared to corn silage alone. This five-season study is representative of continuous corn silage systems in North Central United States, and Wisconsin specifically, distinguished by fall liquid dairy manure applications. Corn was planted after rye termination or harvest, and varying rates of nitrogen were applied to corn. As predicted, rye cover reduced preplant soil nitrate without affecting corn silage yield. Rye harvested as a forage crop reduced preplant and in-season soil nitrate, and total production equaled or exceeded corn silage yields without rye, despite a 13% decrease in corn silage yield. The 5-year nitrogen balance demonstrated almost 40% reduction in excess nitrogen in the rye forage system. This novel study demonstrated no cumulative or single-year agronomic limitations to winter rye implementation in manured, corn silage systems characteristic of North Central United States over a range of seasonal weather conditions. Furthermore, the dual use of rye as a cover crop conservation practice or harvested as a forage double-crop makes it agronomically advantageous and demonstrate potential for sustainable intensification in this system. This research is the first to show that sustainable intensification through double cropping dairy-based systems can increase high-quality biomass production while reducing nitrogen losses to the environment.