A growing number of service learning classes bring students into jails and prisons, stepping across what Alexander (2010) might call the new Jim Crow color line created by mass incarceration. Many of these courses are part of the innovative Inside-Out Prison Exchange Program, which brings inside and outside students together in a shared college class. Drawing on ethnographic observations, interviews, and 8 years of experience teaching Inside-Out courses, this article explores the ways students construct racial identities and understand racial hierarchies as they work together behind bars. Race is the elephant in the room in America's prisons, so faculty need to develop new strategies to support our students in the complex emotional and intellectual work of making sense of race. This requires understanding the diversity of our students' racialized experiences, pushing back against the temptations of colorblindness, and developing new ways to practice relationship building and social solidarity.