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This study explores the role and impact of shadow education at an independent elementary school in Florida. Shadow education has become a common practice in elite environments due to competitive admissions processes and rising academic pressure. Utilizing Bronfenbrenner’s (1979) ecological systems theory, this study investigates the perspectives of students, parents, teachers, and administrators through interviews and one focus group. Findings reveal that tutoring is sought out by parents to support students with academic goals and standardized test preparation, but it also contributes to stress and the normalization of shadow education within elite environments. This study highlights the lived experiences of key stakeholders and encourages reflection on policy, family choices, and the broader impact of shadow education on early academic pressure.