Undocumented immigration has gained unprecedented prominence in many of the world's wealthiest nation-states. In the United States, a substantial population of undocumented youth is growing up with legal access to public education through high school, but facing legal and economic barriers to higher education, even when attaining college admission. The legal and social contradictions associated with undocumented status limit these youths’ chances for upward mobility through traditional means. Based on ethnography and in-depth interviews, this article examines the experiences of documented and undocumented children of working-class Latino immigrants in Los Angeles. Because their educational and home environments are not differentiated, undocumented youth undergo similar social incorporation processes as their documented peers early on. However, their legal protections end after high school, greatly limiting their chances for upward mobility through education. In some cases, knowledge of future barriers to college attendance leads to a decline in educational motivation. Existing assimilation theories need to be expanded to include this novel and sizeable phenomenon.