This article examines how leaders in public, private, and hybrid educational systems manage competing pressures in their institutional environments. Across all systems, leaders responded to system-specific puzzles by (re)building systemwide educational infrastructures to support instructional coherence and framed these efforts as rooted in concerns about pragmatic organizational legitimacy. These efforts surfaced several challenges related to educational equity; leaders framed their responses to these challenges as tied to both pragmatic and moral organizational legitimacy. To address these challenges, leaders turned to an array of disparate government and nongovernment organizations in their institutional environments to procure and coordinate essential resources. Thus, the press for instructional coherence reinforced their reliance on an incoherent institutional environment.