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Educational leadership roles are dominated by men, and women receive lower salaries in administrative positions than their male counterparts. This study examined factors that may be related to the salaries of principals based on data available from Pennsylvania. We conducted three hierarchical linear models with annual salary as the outcome variable. 2,630 principals were organized into 2,438 level two groups (schools) and 498 level three groups (districts). Results confirmed that female principals outnumber males at the elementary level but are underrepresented overall. Male principals are paid more than their female counterparts. Other factors that favor males are predictive of higher salaries as well. These results paint a concerning picture for the current allocation of resources in public education across Pennsylvania.