Double-cropping winter rye cover crops (CC) with soybean in the North Central US could help with the global effort to sustainably intensify agriculture. Studies addressing the management of these systems are limited. Therefore, a field study was conducted from 2017 to 2019 in Central Iowa, US to evaluate winter rye CC biomass production, aboveground N accumulation, estimated economics, estimated within-field energy balance and estimated greenhouse gas (GHG) emissions under three N application rates (0, 60, 120 kg N ha−1) and three planting methods (pre- and post-harvest broadcast and post-harvest drilling). Averaged over N rates, all planting methods resulted in >5.0 Mg ha−1 year−1 rye aboveground biomass dry matter. Averaged over the 2-year study and compared with unfertilized treatments, applying 60 kg N ha−1 produced 1.1 Mg ha−1 more aboveground biomass (6.1 vs 5.0 Mg ha−1), accumulated 30 kg ha−1 more N in aboveground biomass (88 vs 58 kg N ha−1), and led to 20 GJ ha−1 more net energy. Biomass production was not significantly higher with 120 kg N ha−1 compared with the 60 kg N ha−1 rate. Even when accounting for an estimated 0.75 Mg ha−1 of above ground rye biomass left in the field after harvesting, more N was removed than applied at the 60 kg N ha−1 rate. The minimum rye prices over the 2-year study needed for double-cropping winter rye CC to be profitable (breakeven prices) averaged $117 and $104 Mg−1 for the 0 and 60 kg N ha−1 rates, which factors in estimated soybean yield reductions in 2019 compared with local averages but not off-site transportation. GHG emissions were estimated to increase approximately threefold between the unfertilized and 60 kg N ha−1 rates without considering bioenergy offsets. While environmental tradeoffs need further study, results suggest harvesting fertilized rye CC biomass before planting soybean is a promising practice for the North Central US to maximize total crop and net energy production.