The military is a major state provider of employment, occupational training, and educational subsidies. Yet military downsizing and its increased selectivity during penal expansion may have cleaved off employment opportunities for disadvantaged men. We show how institutional castling (the shifting prominence of competing institutions in the lives of specific demographic groups) has affected the underlying risk of military employment and penal confinement. Black veterans who have dropped out of high school are less likely to be incarcerated than their nonveteran counterparts, and declines in the employment rates of military servicemembers with less than a high school education are associated with large increases in incarceration rates. The military’s critical role in providing institutional protection from the penal system has eroded for young, undereducated African American men.