Using Critical Race Theory (CRT) and Latino/a Critical Race Theory (LatCrit) as analytical tools, this article examines the experiences of a seven Latino/a high school students at various points of engagement with the school-to-prison pipeline. Building on and extending Franz Fanon's (1952) concept of the epidermalization of inferiority, the authors demonstrate the nuanced ways that institutional racism and other interrelated forms of oppression function to contribute to a sense of internalized oppression among Latino/a youth. We critically examine the ways in which dialogue and collaborative research undertaken in a supportive classroom atmosphere can help students move from feeling shame and guilt to having an enhanced critical understanding of their experiences with incarceration, including an analysis of their own involvement with the school-to-prison pipeline.