Research suggests that Latino adolescents face challenges with respect to their perceptions of success in academia while falling behind in school competencies. This study examines pathways between parent characteristics, adolescent perceptions of parental academic importance, school connectedness, and academic aspirations/expectations for Latinos using a structural equation model. The entire population of seventh grade students was surveyed in the Oklahoma City Public School District (N = 1,832). The final model included Latino students (N = 661). Results found that 51.1% of all Latino adolescents identified as having an undocumented parent(s). Findings indicate that parental documentation was significantly associated with academic aspirations/expectations beyond being Latino. Parental documentation poses limitations on parents' ability to become actively involved in their adolescents' academics. Findings suggest efforts to increase academic aspirations/expectations should come from adolescent experiences (i.e., school connectedness) as citizenship issues are difficult to mitigate. Results should be used as support for such programs in targeting at-risk Latinos.