To evaluate the limitations of the traditional parenting model in the cultural transition period, this study investigated the relationship between parenting behaviors and adolescents' well-being, in which the moderating role of consistency in parent-adolescent cultural orientation was also investigated. Six hundred forty-four parent-adolescent dyads completed self-report surveys. Parents completed the cultural orientation questionnaire (parental version), and adolescents completed the cultural orientation questionnaire (adolescent version), the adolescent-perceived parenting behavior scale, the adolescent basic psychological needs scale, and the adolescent well-being questionnaire. The findings were as follows: (1) Adolescent-perceived parental autonomy support positively predicted the satisfaction of adolescents' basic psychological needs, thereby enhancing adolescents' well-being levels. Conversely, adolescent-perceived parental control significantly predicted the frustration of adolescents' basic psychological needs, thereby reducing their well-being levels. (2) When both parents and adolescents share a collectivistic cultural orientation, high parental control significantly frustrated adolescents' basic psychological needs, but it did not negatively affect their well-being. However, when parents are collectivists but adolescents are individualists, high parental control would significantly induce the frustration of basic psychological needs, thus further impairing adolescents' well-being. The results revealed that differences in cultural orientations between generations during cultural transition periods moderate the effects of parenting behaviors.