The underlying mechanisms (i.e., linking and conditioning mechanisms) in the association between perceived parental career expectation and adolescents’ career development remain understudied. Under the guidance of the social cognitive career theory, this study used three-wave longitudinal data from 3,196 Chinese adolescents (Mage = 15.55 years old, SD = .44; 52.8% girls at Wave 1) to fill such gaps. Results indicate conditional indirect effects. Specifically, the indirect association of perceived parental career expectation with adolescents’ career adaptability and ambivalence via adolescents’ career-planning and goal-setting self-efficacy was stronger when perceived parent–adolescent career congruence was higher than that when perceived parent–adolescent career congruence was lower. Such effects were identified even after various career-related parenting practices were controlled for. Implications for theory, future research and interventions were also discussed.