Recent public discussions and legal decisions suggest that school segregation will remain persistent in the United States, but increased transparency may help monitor spending across schools. These circumstances revive an old question: is it possible to achieve an educational system that is separate but equal—or better—in terms of spending? This question motivates further understanding the measurement of spending progressivity and its association with segregation. Focusing on economic disadvantage, we compare two commonly-used measures of spending progressivity: exposure-based and slope-based. We show that each measure is predicated on different assumptions about the progressivity of within-school resource allocations, and that they are theoretically linked through segregation. We empirically examine school spending progressivity and its properties using nationwide school spending data from the 2018-19 school year. Consistent with our theory, the exposure-based measure is the slope-based measure shrunk inversely by economic school segregation. This property makes more segregated school districts look more progressive on the exposure-based measure, representing a seemingly “separate but better” relationship. However, we show that this provocative pattern may be reversed by relatively modest poor-versus-nonpoor differences in unobserved parental contributions. We discuss implications for the measurement of progressivity, and for theory on public educational investments broadly.