Relationships between parental behaviors and adolescent self-esteem were analyzed in a group of 95 early adolescents from multiple settings. The study was designed to investigate hypotheses regarding associations between observed parental interactions (e.g., accepting and devaluing) and adolescent self-esteem. Parents' verbal interactions with their adolescents were assessed through application of the constraining and enabling coding system to transcribed family discussions, generated through a revealed differences procedure. Adolescent self-esteem was measured with the Coopersmith Self-Esteem Inventory. Parent interaction-self-esteem associations were examined in the pooled sample, as well as in specific sub-groups based on gender, health, and ego development (measured by the Washington University Sentence Completion Test). Boys had more numerous associations between their self-esteem and parental interactions than girls, and psychiatrically ill boys had particularly high associations. Parental interactions were found to be most strongly related to adolescent self-esteem for adolescents at the lowest levels of ego development. Our findings are consistent with the view that increasing individuation in self-esteem regulation occurs during adolescent development, such that adolescents at higher levels of ego development evaluate themselves more independently of parental feedback than do their less mature peers.