Parenting behaviors have been linked to children's self regulation, but it is less clear how they relate to adolescent psychological flexibility. Psychological flexibility is a broad construct that describes an individual's ability to respond appropriately to environmental demands and internal experiences in the service of their goals. We examined the longitudinal relationships between perceived parenting style and psychological flexibility among students at five Australian schools (N = 749) over 6 years, beginning in Grade 7 (50.3% female, mean age 12.39 years). Parenting style was measured in Grades 7 and 12, and psychological flexibility from Grade 9 through 12. Psychological flexibility decreased, on average, with age. Multi-level modelling indicated that authoritarian parenting (low warmth, high control) in Grade 7 predicted later (low) psychological flexibility. Moreover, increases in authoritarian parenting and decreases in authoritative parenting (high warmth and control) were associated with adolescent psychological flexibility across the high school years. Change in parenting predicted future psychological flexibility but did not predict change over time. Structural Equation Modelling revealed that adolescent psychological flexibility in Grade 9 predicted later decreases in authoritarian and increases in authoritative parenting. We discuss the implications of these findings for understanding how parenting changes and the consequences of such change for the development of psychological flexibility.