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This paper explores how students at Seascape High School in south Florida navigated their roles as mentors. Emerging from a larger multi-level case study, researchers conducted two focus group interviews with student mentors in February 2020. We found that mentors used their insider knowledge as students to inform their interactions with mentees. They described themselves as the anti-authority, utilizing their positions as student mentors to facilitate the transition process for incoming 9th grade mentees by becoming their supporters and informants. The data also revealed the influence of school organization on the capacity of mentors to perform their roles as desired, suggesting that the success of peer mentorship programs depend on the collaboration of student mentors, administrators, teachers, and other stakeholders.