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This study examines the micropolitics of voluntary unionization among charter management organizations (CMOs) using an ecological-political framework. Through a comparative qualitative cross-case study of four CMOs in two metropolitan areas, we explore how teachers navigate unionization, how CMOs respond to organizing efforts, and what political strategies actors deploy. Findings reveal a spectrum of working relationships, from combative to collaborative, influenced by contextual factors, strategic choices, and stakeholder power dynamics. Early unionization efforts are marked by combative relationships, while established unions tend to have more collaborative interactions, albeit strained during bargaining. The study highlights the complex nature of charter school unionization, demonstrating how different goals, strategies, and power dynamics lead to diverse outcomes.