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In this study, we investigate the evolving role of assistant principals (APs) and how principals allocate leadership responsibilities in schools with multiple APs. Drawing on interviews with central office staff, principals, and APs in two large urban districts, the study explores how AP tasks are distributed and aligned with school needs and leadership development goals. Findings reveal significant growth in the number of AP positions and increasing reliance on APs for instructional leadership, student support, and school administrative management. Principals often tailor AP roles to individual strengths and career aspirations. This paper highlights the strategic allocation of APs to specific school leadership roles and offers insights for improving principal preparation and succession planning through more intentional role design and support.