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This qualitative study explores how professional development (PD) supports instructional leadership, quality, and equity in the principalship. Research questions were: What types of PD do principals and principal supervisors find most useful for developing instructional leadership skills? What are benefits and challenges of participating in PD designed for the principalship? Five elementary principals, four secondary principals, and three principal supervisors from two school divisions in a southeastern U.S. state were interviewed. Regarding findings, principals reported that their PD experience built capacity for teaching and learning and networks; while some could choose among PD topics, constraints limited everyone’s involvement. Principal supervisors used evidence-based practices/data to determine principal PD opportunities. The findings could help catalyze quality principal-specific PD for impacting student achievement.