In high school writing centers that employ students as tutors, staff members can face challenges as they transition into a tutorial role. This study of how tutors in a student-staffed high school writing center perceive their tutorial identities revealed that such work empowered participants in deep and transformative ways but also complicated participants’ perceptions of their roles as students, writers, and tutors. Through their tutorial training, participants came to understand alternate ways of learning and teaching. This new lens interrupted what they had previously perceived as “normal” school-based writing and writing instruction. In a role they perceived as misunderstood, tutors reported struggling to educate others about collaborative tutoring. In addition, participants voiced significant reservations about clients’ and teachers’ attitudes towards writing and about what they felt was overly directive writing instruction in their school. Therefore, while tutorial identity empowered student tutors, the institutional climate also constrained them.