The potential mediating role of career-related parenting practice in the association between parental career expectation and adolescents’ career development remains understudied, especially the likely transactional dynamics inherent within such links. This study utilized three-annual-wave data from 3196 Chinese adolescents across the high school years (M = 15.55 years old, SD =.44; 52.8% girls at Wave 1) to address such gaps. Results of cross-lagged structural equational modeling analyses demonstrated reciprocal associations between parental career expectation and career adaptability consistently across three high school years; and career-related parental support served as a mediator in such associations, net of a series of covariates. However, no associations of career ambivalence with parental career expectation across the high school years emerged. Such findings highlighted the dynamic nature of the associations among parental career expectation, career-related parenting practice, and adolescents’ career developmental outcomes. Implications for future research and practice were discussed.