Secondary literacy instruction often happens to adolescents rather than with them. To disrupt this trend, we collaborated with 12th-grade literacy mentors to reimagine literacy teaching and learning with 10th-grade mentees in a public high school classroom. We used positioning theory as an analytic tool to (a) understand how mentors positioned themselves and how we positioned them and (b) examine the literacy practices that enabled and constrained the mentor position. We found that our positioning of mentors as collaborators was taken up in different and sometimes unexpected ways as a result of the multiple positions available to them and institutional-level factors that shaped what literacy practices were and were not negotiable. We argue that future collaborations with youth must account for the rights and duties of all members of a classroom community, including how those rights and duties intersect, merge, or come into conflict within and across practices.