Latina/o high school students without documentation face a challenging situation when they graduate from high school, with pathways to work and postsecondary education stymied by their immigration status. We examined the effects of anticipated barriers associated with immigration status, age, and sex on the dependent variables of vocational outcome expectations, anticipated external and internal barriers, and postsecondary schooling plans in a sample of 475 Latina/o high school students. Findings include that students anticipating immigration status problems had lower vocational outcome expectations and anticipated more external barriers to pursuing their postsecondary plans. Latina girls and older high school students anticipating immigration status problems were more likely to plan to attend 2-year rather than 4-year colleges, and less likely to plan on postsecondary education, respectively. Implications for practice, policy, and research are discussed.