Second-generation Latin-American adolescents tend to show higher levels of various health-risking behaviors and emotional problems than first-generation Latin-American adolescents. This cross-sectional study of 40 mother-adolescent dyads examined the association of mother-youth acculturation gaps to youth adjustment problems. Intergenerational acculturation gaps were assessed as a bidimensional self-report component and a novel observational measurement component. The Latin-American adolescents were predominantly second-generation of Mexican descent (M age = 13.42 years, SD = 0.55). Most of the mothers were born in Mexico (M age = 39.18 years, SD = 5.17). Data were collected from mothers, adolescents, and coders, using questionnaires, structured interviews, and videotaped mother-youth interaction tasks. Findings revealed generally weak support for the acculturation gap-distress hypothesis. In addition, stronger relative adherence to their heritage culture by the adolescents was significantly (p < .05, ES = 0.15) related to less engagement in early health-risking sexual behaviors, possibly reflecting selective acculturation processes. Mother-youth acculturation gaps in orientation to the heritage culture were the most salient dimension, changing the focus on the original formulation of the acculturation gap-distress hypothesis.