The past three decades of terrestrial remote sensing research have delivered unprecedented insights into our fundamental ability to detect, quantify, and differentiate plant disease (Gold 2021). However, much of our fundamental knowledge in this domain has come from studies in non-agricultural systems and until recently, most agricultural studies, when extant, have focused on tree crops where canopy closure and large plot and plant size facilitate stress detection at low spatial resolution. Recent engineering innovations and advancements in constellation architecture design have refined the accuracy and scalability of airborne and spaceborne sensing platforms, enabling us to monitor diverse specialty crops, including grapevine, planted in smaller, spatially varied fields.