Parental depression has been identified as a risk factor for children's and adolescents' internalizing problems. In the current study, we aimed to investigate the role of maternal parenting behaviors (i.e., responsiveness and autonomy-support) and adolescents' representations of attachment to their mother (i.e., anxiety and avoidance) in the intergenerational similarity of internalizing symptoms. The sample was heterogeneous and consisted of referred (42%) and non-referred adolescents (N = 238, 31% female) and their mothers. Both adolescents and mothers reported on internalizing symptoms, parenting behaviors and all adolescents reported on mother-child attachment. Results showed that parenting behaviors and mother-adolescent attachment explain at least part of the intergenerational congruence of internalizing symptoms. Moreover, there were meaningful and specific associations between dimensions of parenting and dimensions of attachment. Higher responsiveness was primarily related to lower avoidance and higher autonomy-support was primarily related to lower anxiety. The current study's results suggest that maternal depressive symptoms relate to maladaptive parenting strategies and insecure attachment representations in adolescents. Further, both attachment anxiety and avoidance seem to relate positively to adolescents' internalizing symptoms. Targeting both parenting and attachment may form a fruitful approach to prevent and treat internalizing problems in adolescence.