In this qualitative case study, we used the framework of positioning to show how college-age tutors and their middle school tutees interact in an afterschool tutoring setting with regard to ability. The authors show how educational tracking and understandings of disability permeated tutoring spaces and influence tutors' instructional decisions. Even though the tutors' participation in this program was framed as an act of social justice, the tutors do not feel empowered to use a critical lens when discussing tracking and/or disability because, as the authors posit, the framing of the college students as role models and these middle school students as "needy" prohibits conversations that do not have easy answers.