The current study prospectively examined hypothesized short- and long-term reciprocal relations between perceived parental knowledge and adolescent heavy episodic drinking, marijuana use, and delinquency. Using the contextual model of parenting style (Darling & Steinberg, 1993), we examined the extent to which the bidirectional nature of associations between knowledge and adolescent outcomes is dependent on a facet of parenting style: the quality of the parent-child relationship. Data came from the first 4 waves of the National Longitudinal Study of Youth 1997. The sample for the current study consisted of 5,419 students between 12 and 14 years of age at baseline (52% male) surveyed annually for 4 years. Parallel process, autoregressive latent trajectory models were used to examine relations between initial levels and change over time in perceived parental knowledge and adolescent risk, and short-term cross-lagged paths were included to examine bidirectionality while accounting for long-term associations. Results showed significant short-term and long-term bidirectionality between perceived parental knowledge and adolescent outcomes, with parent effects on students and student effects on parents. Long-term associations across constructs were negative, whereas short-term associations were positive. These reciprocal associations were shown to differ across levels of parent-child relationship quality with regard to adolescent heavy episodic drinking and delinquency, providing support for the contextual model of parenting style. Implications for future work on parent-child bidirectional relationships and parent-based interventions are discussed.