Grassland birds are among the most imperiled groups of birds in North America. Conversion of native prairie to cropland and developed areas, rangeland deterioration, and fragmentation have contributed to precipitous losses in obligate grassland bird species. Since the mid-1800s, >80% of grassland ecosystems have been lost in North America. One species sensitive to the degradation of grassland types is the Upland Sandpiper (Bartramia longicauda), which can serve as an indicator species for prairie sustainability and has experienced a 4.5% decline in numbers in the eastern United States since 1966. We assessed scientific literature for the Upland Sandpiper from 1886 to 2022 to identify historical and potential future threats, describe breeding habitat limiting factors, and evaluate breeding habitat management strategies that can effectively conserve the Upland Sandpiper across the Great Plains region of North America. Using this data, we constructed a hierarchical model of Upland Sandpiper nest site preferences to better understand their habitat ecology and guide habitat management. Upland Sandpipers use short, mixed, and tallgrass prairie, jack pine (Pinus banksiana) barrens, cropland, peatlands, and alpine ridges for breeding. Historical land management practices in the Great Plains region of the United States have left once-suitable Upland Sandpiper habitat increasingly fragmented and often with unsuitable composition and/or structure for breeding. Prairie should be managed for a mosaic of vegetation heights by burning 20–30% of grassland area annually in March–April, or by grazing cattle year-round at 3.2–4.6 ha per animal unit. These conservation strategies should provide grassy vegetation 15–30 cm tall for nesting in May interspersed with patches of vegetation <10 cm tall for feeding and successful brood-rearing. Habitat management for the structural and compositional habitat requirements of Upland Sandpiper can benefit more than 90 grassland bird species.