<p>Empirical research examining the associations between adolescents’ risk-taking behaviors and academic development has relied predominantly on cross-sectional designs, which are insufficient to disentangle the complex dynamic associations between positive and negative risk-taking behaviors and academic development among adolescents, particularly in China. Using a four-wave longitudinal design, this study examined the dynamic directional associations between positive and negative risk-taking behaviors and academic development (operationalized as academic engagement and academic achievement) in a sample of 672 adolescents (<i>M</i>age = 12.21, <i>SD</i> = 0.87). The results indicated that positive risk-taking behaviors exert a transient negative effect on academic engagement from T2 to T3, but sustained positive effects on academic achievement from T1 to T4, with a bidirectional and mutually reinforcing association between positive risk-taking behaviors and academic achievement from T3 to T4. In contrast, academic engagement consistently negatively predicts subsequent negative risk-taking behaviors from T1 to T4, whereas academic achievement has limited negative predictive effects on such behaviors from T1 to T2. Moreover, negative risk-taking behaviors adversely predict both academic engagement and academic achievement, establishing a bidirectional and mutually deteriorating association with academic engagement from T3 to T4 and forming a vicious cycle with academic achievement from T1 to T3. These findings highlight that the associations between adolescents’ positive and negative risk-taking behaviors and academic development are dynamic and time-varying. The present study contributes to the growing body of literature on facilitating adolescents’ academic development within the positive risk-taking framework and provides evidence-based implications for mitigating negative risk-taking behaviors by targeting improvements in academic development.</p>