Background and Purpose: District school improvement efforts have increasingly focused on improving the quality of support principals receive from the central office. This study uses the theoretical lens of recoupling to examines efforts by one urban district in the midst of change to revise the role of principal supervisors. Analysis focuses on how district organizational structures and systems supported (or did not support) principal supervisors' work in the new role. Research Methods: This qualitative study draws upon semi-structured interview data from 31 principals, principal supervisors, and central office leaders. Data were analyzed using an iterative, multi-round coding process that identified emergent themes. Findings: District central office structures, systems, and roles shape principal supervisors' ability to effectively develop principal leadership. System-wide changes to support principal supervisors' new work appeared to be at odds with existing district context and structure, limiting their effectiveness. Additionally, three organizational barriers emerged that limited principal supervisors' ability to meet the new role expectations: misaligned central office expectations, overlapping responsibilities between supervisors and other central office administrators, and an incoherent district definition of instructional leadership. Implications: Findings provide guidance for districts seeking to build central office capacity for school support by highlighting the importance of implementing district-level structural supports and other system considerations in addition to changing administrator roles.