Internalizing symptoms, such as depressive and anxiety symptoms are prevalent in adolescence. We examined the mediational role of two self-esteem dimensions, that is, level and contingency, in comprehensive models linking parenting to adolescent internalizing symptoms. Using a cross-sectional design, a large sample of secondary school students (N = 1958; 56.28% female; mean age = 15.31 years) completed questionnaires on maternal responsiveness, psychological control, conditional regard, as well as on their own self-esteem, depressive and anxiety symptoms. Analyses yielded both direct and indirect effects of adolescent-reported parenting on internalizing symptoms. More perceived responsiveness was uniquely associated with higher self-esteem level which, in turn, predicted less depressive and anxiety symptoms. Perceived conditional negative and positive regard and psychological control were uniquely related to self-esteem level (negative relations) and contingency (positive relations) which, in turn, predicted more internalizing symptoms. In general, our study supported the mediational role of self-esteem level and contingency in the link between parenting and internalizing symptoms. Whereas low self-esteem increased adolescents’ vulnerability for both depressive and anxiety symptoms, high self-esteem contingency appeared as a unique vulnerability factor for anxiety symptoms.