Parents and adolescents often hold discrepant views about the family environment and these discrepancies may in turn influence adolescents’ psychological adjustment. The current study examined how adolescent–parent perceptions of family routines and chaos, and their congruence and incongruence, relate to adolescents’ self-reported psychological adjustment (depressive symptoms and perceived stress), both concurrently (N
dyads = 261; 53 % female) and 2 years later (N
dyads = 118; 50 % female). Using polynomial regression and response surface analysis, results indicated that adolescents’ perceptions of the family environment were a stronger predictor of adolescents’ adjustment than parents’ perceptions (76 % mothers), concurrently and over time. However, both congruence and incongruence in adolescent–parent perceptions were also related to adolescents’ adjustment. Specifically, congruently negative adolescent–parent perceptions were associated with worse concurrent adolescent adjustment. Further, incongruence defined by more negativity in adolescents’ versus parents’ perceptions was associated with worse adolescent psychological adjustment, concurrently and over time. In sum, in addition to the strong links between adolescents’ perceptions of the family and their own psychological adjustment, examining how congruent and incongruent adolescents’ perceptions are with parents’ perceptions may shed additional light on how the family environment relates to adolescent adjustment.