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The chapter authors offer that current reform efforts have been designed to focus principal supervisors on supporting and developing the instructional leadership of principals. This chapter reviews the changing role of principal supervision by examining the complexities that underlie the role transformation of principal supervisors in the context of school district central office reform, from a compliance-focused, middle manager in the system hierarchy to a developmental coach in support of principals as instructional leaders. We address tensions among the components of the new and old roles and describe challenges districts may face in redesigning the role raising questions as to the viability and feasibility of effective principal supervision and what it might entail moving forward.