We have spent the last several years using hyperspectral imaging to map plant diversity in grasslands. However, most of our efforts have been limited to small or “highly manipulated” grassland experiments. To assess its potential, it is critical that we test hyperspectral imaging in naturally-assembled grasslands, which have high spatio-temporal variability. Recently, we started using fine-resolution airborne and coarse-resolution spaceborne hyperspectral data and asked whether these data can capture plant diversity in naturally-assembled grasslands. Through these efforts, it is our hope to provide a first-cut look at the potential of forthcoming spaceborne imagers, such as SBG, for monitoring grassland diversity.