The practice of planting winter cover crops has seen renewed interest as a solution to environmental issues with the modern maize- and soybean-dominated row crop production system of the US Midwest. We examine whether cover cropping patterns can be assessed at scale using publicly available satellite data, creating a classifier with 91.5% accuracy (.68 kappa). We then use this classifier to examine spatial and temporal trends in cover crop occurrence on maize and soybean fields in the Midwest since 2008, finding that despite increased talk about and funding for cover crops as well as a 94% increase in cover crop acres planted from 2008–2016, increases in winter vegetation have been more modest. Finally, we combine cover cropping with satellite-predicted yields, finding that cover crops are associated with low relative maize and soybean production and poor soil quality, consistent with farmers adopting the practice on fields most in need of purported cover crop benefits. When controlling for invariant soil quality using a panel regression model, we find modest benefits of cover cropping, with average yield increases of 0.65% for maize and 0.35% for soybean. Given these slight impacts on yields, greater incentives or reduced costs of implementation are needed to increase adoption of this practice for the majority of maize and soybean acres in the US.