Globally, grasslands have been heavily degraded, more so than any other biome. Grasslands of the eastern U.S. are no exception to this trend and, consequently, native biota associated with the region’s >20 million ha of agricultural grasslands are under considerable stress. For example, grassland associated breeding bird populations have declined precipitously in recent decades as have numerous species of pollinators. Although there is increasing awareness of the role grasslands can play in global carbon cycles and in providing high quality dietary proteins needed by an increasing global population, there is a lack of awareness of the alarming trends in the sustainability of the native biota of these ecosystems. Here, we present the status of this conservation challenge and offer prospective solutions through a working lands conservation approach. Such a strategy entails maintaining appropriate disturbances (i.e., grazing, fire, and their combination), improved grazing management, an increased reliance on native grasses and forbs, and improved plant diversity within pastures. Furthermore, we note some examples of opportunities to achieve these goals, offer suggestions for agricultural and conservation policy, and provide a framework for evaluating tradeoffs that are inevitably required when pursuing a multi-purpose grassland management framework.