The important role of parenting is widely acknowledged, but as most studies have understood and examined it as a stable attribute (e.g., parenting style), the stability of and changes in parenting are less well understood. Using longitudinal person-oriented approaches (i.e., latent profile analyses and latent transition analyses), this study aimed to examine the stability of and changes in autonomy-related parenting profiles and their effects on adolescents’ academic and psychological development. Four autonomy-related dimensions (i.e., autonomy support, warmth, psychological control, conditional regard) were chosen to identify parenting profiles on the basis of Self-Determination Theory. Using five-year longitudinal data from 789 German secondary school students (50.06% female, Mage at T1 = 10.82 years, age span = 10–17), four autonomy-related parenting profiles were found: Supportive (~17%), Controlling (~31%), Unsupportive-Uncontrolling (~17%), and Limited Supportive (~35%). The results suggest that the Supportive profile contributes to adolescents’ positive academic and psychological development, whereas the Controlling profile, which thwarts autonomy development, exacerbates the development of psychopathology, and impairs academic achievement. More importantly, the Limited Supportive profile is as maladaptive as the Unsupportive-Uncontrolling profile. Regarding parenting profiles’ stability and changes, the results showed that about half of each profile stayed in the same group. Overall, it could be observed that parents became more supportive and less controlling over time. However, the findings also indicate that parenting profiles are less stable than expected and can still change during early-to-mid adolescence.