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Today, student teachers are learning to teach amid a complex web of policies, in schools under performance pressure. Yet they are usually left alone to make sense of the relationships between what they learn in teacher education, and what they are allowed to do in their placement schools. University-based supervisors are uniquely positioned to help pre-service teachers interrogate schools’ policy environments; however, they are rarely encouraged to do so. This qualitative study describes a first-time University supervisor’s efforts to support student teachers in questioning the taken-for-grated arrangements between policy and practice in their placement schools. Findings indicate that University supervisors can support student teachers’ navigation of policy and practice, with deep contextual knowledge, and critical, collaborative supervisory frameworks.