In developmental psychology, developing a sense of autonomy is claimed to be an important goal for adolescents. Nevertheless, the question of whether autonomy is always positive for adolescents is a highly debated issue. The goal of this review paper is to provide an overview of research distinguishing between two definitions of autonomy (autonomy as independence, and autonomy as self-endorsed functioning), and how this distinction helps understanding under which conditions autonomy is positive for adolescent development. Further, this paper discusses how this distinction also helps clarifying under which conditions parental rule-setting is effective or not. That is, we argue that it is important to consider the parents’ communication style (i.e., autonomy-supportive or controlling), for understanding whether adolescents will be more likely to accept or reject parental rules.