Despite the well-established associations between adolescents’ internalizing symptoms and career development, it still remains unclear whether adolescents’ internalizing symptoms are precursors or consequences of their career adaptability/ambivalence. Subtler nuance inherent within such association also await to be revealed, because internalizing symptoms and career development have been primarily treated as broad constructs, despite the multifaceted nature of both. To narrow such gaps, this study examined the potentially dynamic associations among career adaptability, career ambivalence, and internalizing symptoms using three-wave longitudinal data. The study collected data from 3196 Chinese adolescents (52.72% girls, mean age = 15.56 years, SD = 0.58) at Wave 1, with 2820 (attrition rate = 11.76%) participating in Wave 2 and 2568 (attrition rate = 8.93%) in Wave 3. The measurement invariance suggested that there were no significant differences across both waves and genders. This study approached associations at both broader construct levels and subtler dimension levels. Results of cross-lagged path models at broader construct levels demonstrated a unidirectional association between internalizing symptoms and career adaptability. Results of models at subtler dimension levels indicated a series of transactional links over time between career adaptability dimensions/ambivalence and depressive symptoms in particular. Career adaptability dimensions and career ambivalence predicted later anxiety symptoms rather than the reverse. Group model comparisons showed no difference across waves and genders. These findings shed light on the dynamic nature of the associations during adolescence between career adaptability/ambivalence and internalizing symptoms, particularly at subtler dimensional levels, which should be considered in relevant clinical and educational practices.