Transitioning from the expansion of croplands to sustainable agricultural intensification is key to ensuring food and nutrition security. This is particularly the case for small-scale subsistence farmers in drylands, where our current understanding on the sustainability of this transition is however mostly derived from theories based on local observations. Here we demonstrate that a new generation of satellite data and computer science technology can be used to set a new baseline to understand the interplay between population pressure and agricultural intensification. By characterizing cropping systems across the African Sahel, we evidence that agroforestry areas of high land use intensity are associated with both high rural population density and crop growth rate, upholding Boserup’s theory of agricultural intensification. Our approach provides the foundation for sustainable agricultural intensification in drylands and represents a pathway towards the integration of multidimensional cropland maps into context-specific policymaking for low- and middle- income countries.