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While research has documented how federal, state, and local policies can limit English Learners’ access to rigorous content coursework, less attention has been paid to the institutional mechanisms that promote or hinder such access, and to school administrators’ roles. This paper reports on a multiple-case study documenting how two high school administrative teams grappled with how to advance equity for ELs with widely different backgrounds and language development profiles. Bringing together institutional theory and social justice leadership theory, we unpack how these school leaders—who held similar stated commitments to quality education for ELs and understandings of the importance of integrating language and content instruction—made choices that both reflected institutional constraints and attempted to leverage existing policy contexts.