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This qualitative paper uses the lens of recoupling to examine the ways in which the district central office supports the work of principal supervisors in developing principals. Data are drawn from 41 semi-structured interviews with central office officials, principal supervisors, and principals in a mid-size urban school district. After an open, iterative coding process, two main findings emerged: (1) The district clearly communicated a vision for principal support through principal supervisors but struggled to implement this vision; and (2) The work of principal supervisors was not clearly defined or differentiated from other central office roles. This paper contributes first-hand insight for leaders and policymakers seeking to improve the overall support that principals receive from the central office.