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This study explores the ways in which school leaders’ capacity to operate as street-level policymakers enables them to understand and meet the needs of immigrant students in North Carolina. Utilizing portraiture, the study provides an in-depth examination of two school leaders in relation to the street-level policymaking framework. Findings show that policy awareness, communal understanding, knowledge of the student population, and shared student positionality, are essential in building street-level policymaking capacity. Implications include the need to diversify school personnel, invest in parental and community outreach, conduct policy and cultural competency trainings, and increase school leaders’ autonomy by removing institutional constraints.