This paper is based on a study on the effects of unauthorized migration on Latino children and youth’s access to education, healthcare, and livelihoods. The research project aimed at improving understanding of the many nuanced effects of undocumented status on employment and livelihood prospects of Latino youth. Research involved ethnographic fieldwork in three neighborhoods in the larger Washington, DC metropolitan area: Chirilagua, VA, a neighborhood on the border of Alexandria and Arlington in northern Virginia; Langley Park, MD; and Columbia Heights, in DC. In this article we attempt to explore the circumstances faced by Latino youth as they transition into adulthood and analyze the effects of unauthorized status of the young person or other family members on incentives to work and access to the labor market. We argue that while these youth are often pressured to choose waged employment over education in order to contribute to the family’s income, their lack of legal immigration status is an incentive to stay in school for the relatively safe legal environment it affords. Once the decision to work has been made, or graduation from high school has forced them out of the safety net, the limited options for work available to these youth create difficult decisions wherein some seek work in safe environments for less compensation while others choose more formal, higher-paying positions that come with exposure and high risk.