Educational transitions involve a number of changes for adolescents and can be challenging for adolescents and parents alike. The present study was designed to gain a better understanding as to how adolescents' perceptions of parenting evolves across a major educational transition and how the parenting perceived across this transition may facilitate adolescents' psychosocial adjustment and identity formation. Swiss adolescents (N = 483, M[subscript age] = 14.96 years old; 64.6% female) in their last year of mandatory secondary school completed self-report measures at two semiannual time points both prior to and following their educational transition. Adolescents reported on their perceptions of their parents' autonomy support and psychological control as well as their self-esteem, risk-taking behaviors, and identity processes. Group-based trajectory analyses identified three parenting trajectory classes (i.e., Highly Supportive Parenting, Decreasing Supportive Parenting, Stable Controlling Parenting), three psychosocial adjustment trajectory classes (i.e., Low Self-Esteem/Low Risk-Taking, High Self-Esteem/Low Risk-Taking, Moderate Self-Esteem/Increasing Risk-Taking), and four identity trajectory classes (i.e., Lost Searchers, Guardians, Pathmakers, Successful Searchers). These solutions support the contention that adolescents are likely to experience academic transitions differently, whether in terms of their parent-adolescent relationship, their psychosocial adjustment, or their identity. Furthermore, parenting trajectory classes were associated with specific identity and psychosocial adjustment classes. Notably, Highly Supportive Parenting was associated with the High Self-Esteem/Low Risk-Taking class and the Pathmaker identity class, whereas Stable Controlling Parenting was most strongly associated with the Low Self-Esteem/Low Risk-Taking class and the Lost Searcher identity class. These findings highlight the importance of autonomy supportive parenting for adolescent development during educational transitions.