Of all terrestrial biomes, grasslands are losing the most biodiversity the most rapidly, and one of the leading causes of grassland losses is woody plant encroachment. There is a critical need to identify remaining “core” grasslands and track outcomes of grassland restoration. However, quantifying outcomes from grassland restoration has historically been challenging due to the lack of tools to rapidly map and track core grassland habitats and grassland biodiversity responses to management. New remote sensing metrics that track boundaries between grasslands and woodlands at annual temporal scales have strong potential for identifying grassland cores, tracking grassland management outcomes, and serving as proxies for grassland biodiversity. Here, we discuss these metrics and projects that test these metrics on Greater Prairie-chicken lek site selection, grassland bird community movements, and responses to prescribed fire treatments in ecosystems ranging from the tallgrass prairies of Kansas to restored grasslands and savannas in Arkansas.