Research has shown that parents' perceived parental self-efficacy (PSE) plays a pivotal role in promoting their children's successful adjustment. In this study, we further explored this issue by comparing psychosocial adaptation in children of parents with high and low PSE during adolescence. One hundred and thirty Italian teenagers (55 males and 75 females) and one of their parents (101 mothers and 29 fathers) participated in the research. Data were collected at T1 (adolescents' mean age = 13.6) and T2 (mean age = 17.5). Parents reported their PSE at T1. At T1 and T2, adolescents reported their perceived academic self-efficacy, aggressive and violent conducts, well-being, and perceived quality of their relationships with parents. At T2, they were also administered questions by using Experience Sampling Method to assess their quality of experience in daily life. As hypothesized, adolescents with high PSE parents reported higher competence, freedom and well-being in learning activities as well as in family and peer interactions. They also reported fewer problematic aspects and more daily opportunities for optimal experience. Findings pointed to the stability of adolescents' psychosocial adaptation and highlighted possible directions in future research.