This study examined longitudinal acculturation patterns, and their associations with family functioning and adolescent risk behaviors, in Hispanic immigrant families. A sample of 266 Hispanic adolescents (Mage = 13.4) and their primary parents completed measures of acculturation, family functioning, and adolescent conduct problems, substance use, and sexual behavior at five timepoints. Mixture models yielded three trajectory classes apiece for adolescent and parent acculturation. Assimilated adolescents reported the poorest family functioning, but adolescent assimilation negatively predicted adolescent cigarette smoking, sexual activity, and unprotected sex indirectly through family functioning. Follow-up analyses indicated that discrepancies between adolescent and parent family functioning reports predicted these adolescent outcomes. Results are discussed regarding acculturation trajectories, adolescent risk behavior, and the mediating role of family functioning.