Psychiatric illness in adolescence is associated with long-term impairments, making it critical to identify predictors of adolescent psychiatric distress. Individual differences in stress sensitivity could be associated with longitudinal trajectories of internalizing symptoms. Historically, researchers have operationalized stress sensitivity by assessing either objective or subjective responses to stress. However, we posit that the relative discordance between subjective and objective responses to stress is a critical metric of stress sensitivity. We examined whether two discordance-based indices of stress sensitivity were related to one another and to trajectories of internalizing psychopathology among a sample of 101 adolescent youths (M = 12.80 at baseline; 55% males) across two successive stressors: the high school transition and the COVID-19 pandemic. Using latent growth curve modeling, we found that greater discordance between subjective (i.e., affective) and objective (i.e., cortisol) responses to a social-evaluative stressor was associated with higher internalizing symptoms at baseline and an accelerated symptom growth trajectory across the first year of the pandemic. In contrast, early life stress sensitivity was not associated with internalizing symptoms. Findings suggest that the discordance between objective and subjective experiences of social-evaluative stress predicts a pernicious growth trajectory of internalizing symptoms during adolescence. This work advances current methodologies, contributes to theoretical models of internalizing psychopathology, and with replication could have implications for policy and practice by identifying a key vulnerability factor that increases adolescents' psychiatric distress over time.