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Research on teacher collective bargaining agreements (CBAs) documents that negotiated agreements impact school district functioning and student outcomes. However, little is known about how teacher CBAs are actually implemented on a daily basis in schools. In this study, I draw on sensemaking theory to explore how principals’ interpretations, understandings, and beliefs influence their implementation of a CBA in an urban school district. Based on interviews with seven principals, I argue that the cognitive structures, social, and political context of principals, coupled with the language of the contract impact the ways in which CBAs are implemented. The findings add to understandings of CBA implementation by documenting the varied roles school principals play in shaping how contractual provisions effectually operate in schools.