We speak with Dan Callahan, Assistant Superintendent for Secondary Education in Peekskill City School District, 45 minutes north of Manhattan. The low-income district in wealthy Westchester is 70% Latino, including many students from immigrant families. We discuss how the district has adapted to rapid demographic changes and schools' role in helping students meet challenges. Mr. Callahan reflects on the decisions he and his staff make that impact students’ lives in very concrete ways, and the tension between consistency, applying the same rules for all students, and specificity, looking at the totality of circumstances in each individual case.