Mass incarceration and its impact on communities and families has received considerable attention in the news media. Over time, the United States has become a world leader in the percentage of the population serving time in prisons, with a disproportionate number coming from African American neighborhoods. Lying underneath the situation is a prison–industrial complex of public and private organizations that serve this vast marketplace in diverse ways. However, for reasons that have roots in historical race relations in the United States, women and men serving prison sentences have become key components in a system that drives profitability for private companies but often fails to consider inmates’ intricate set of needs or their rehabilitation. This case chronicles the introduction of a new district sales manager to the prison market space, as she learns about and confronts the role of her firm in this conundrum.