AbstractHarvesting annual winter cereal rye (Secale cereale L.) (WCR) as an emergency forage could offset cover crop establishment costs, facilitate WCR adoption, and still provide multiple ecosystem benefits. A five site‐year trial was conducted in Colorado (CO) and Illinois (IL) to evaluate the effect of harvest date on WCR forage yield, quality, and its economic performance. From March to April, WCR dry matter (DM) yield increased exponentially in CO and linearly in IL. The DM yield at Julian day (DOY) 112–116 in CO was 6.9, 5.0, and 5.2 Mg ha–1 in 2018, 2019, and 2020, respectively, compared with 4.7 and 2.7 Mg ha–1 in IL in 2019 and 2020, respectively. Delayed harvesting increased acid detergent fiber and neutral detergent fiber concentrations and decreased crude, total digestible nutrients, and relative feed quality. Yield–quality trade‐off showed that forage yield increased rapidly but forage quality declined after DOY 105–108. Economic analysis, including cost of nutrient removal and 10% cash crop (corn [Zea mays L.]) yield penalty following WCR production revealed harvesting WCR biomass as forage was economically feasible in four out of five site‐years at hay price over $132 Mg–1. Eliminating corn yield penalty indicated profitability in four site‐years at hay price of ≥$110 Mg–1 and removing nutrient removal costs made all site‐years profitable at hay price of ≥$110 Mg–1. It was concluded that harvesting WCR biomass can be a profitable and effective strategy for sustainable intensification that can offer environmental stewardship and economic benefit.