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This paper investigates the challenges of conducting social justice-oriented policy inquiry with youth. It applies differing notions of positionality: the researcher’s positionality in relation to study participants (Milner, 2007), and participants’ social and organizational positionality as policy actors (Ball et al., 2012). These concepts ground an analysis of the research methods used in a two-year case study of youth enactment of competitive high school choice policy. Positionality proved relevant to all stages of empirical inquiry. Researcher and policy actor positionality intertwined, shaping study development, data collection and analysis. Additionally, researcher awareness of policy actor positionality was instrumental to school and student sampling. Implications are drawn for rigorous research that empowers participants and informs efforts to promote policy equity.