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The influence of teachers’ unions on schooling cannot be overstated. Collective bargaining shapes levels of critical educational resources and outcomes. Qualitative inquiry finds that contract language and school-level social dynamics shape the fidelity of collective bargaining agreement implementation. These elements are shown to provoke conflict or support collaboration among school agents. Yet little is known about the dynamics amid district and union representatives at the negotiation table. This study describes the black box of collective bargaining in a large urban district. Drawing on interview data, we employ structure-agency theory to interpret how social dynamics amid district and union representatives shape the contract’s provisions and language, with implications for school-level outcomes.