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Informant discrepancies between parents and adolescents have been increasingly recognized as a meaningful construct with demonstrated implications for treatment outcomes in clinical populations. However, less is known about their relevance to adolescent adjustment in community samples, their domain-specific associations across internalizing and externalizing problems, and the role of family functioning in these associations. This exploratory study examined whether parent-overreporting versus adolescent-overreporting of adolescents' internalizing and externalizing problems was associated with adolescent adjustment, and whether family functioning indicators were involved in these associations. Using dyadic data from 1,696 parent-adolescent dyads in the UK Millennium Cohort Study, Wave 7, structural equation modeling was conducted to examine direct and indirect associations between discrepancy direction and adolescents' mental health problems and substance use behaviors, including smoking, binge drinking, and drug use. Four family functioning indicators were examined: parent-adolescent communication, emotional closeness, parental knowledge, and parental control. Results showed that parent-overreporting, relative to adolescent-overreporting, was associated with more favorable adolescent adjustment, but the pattern differed by discrepancy domain. Internalizing-based parent-overreporting was mainly associated with fewer mental health problems, whereas externalizing-based parent-overreporting was associated with both fewer mental health problems and lower likelihoods of smoking, binge drinking, and drug use. Communication and closeness were more consistently involved in indirect associations with mental health problems across both discrepancy domains, whereas parental knowledge was more clearly involved in indirect associations with substance use outcomes in the externalizing discrepancy model. These findings suggest that discrepancy direction provides adjustment-relevant information in community samples and that its implications depend on the problem domain assessed and the family functioning indicators considered. The study contributes to multi-informant assessment by supporting a domain-specific and relational interpretation of parent-adolescent discrepancies in adolescent psychological difficulties.