Adolescents with internalizing problems are more prone to feelings of guilt and shame, experience more guilt-induction, and report more negative parenting, but little is known about the way these processes are associated nor the extent to which they occur within real-time parent-adolescent interactions. The current study sought to clarify these links by investigating whether negatively biased perceptions of maternal communication mediate links between adolescent internalizing symptoms and their feelings of guilt, shame, and guilt-induction during real-time mother-adolescent discussions. One hundred twenty-three mother-adolescent dyads participated in the study. These dyads were moderately diverse in both race/ethnicity (53% White, 29% Black, 12% Hispanic) and family income (26% earned less than $30,000/year, 22% earned more than $100,000/year) and included adolescents who ranged in age from 12 to 17 (Mage = 13.99) and were approximately half female (54%). Mothers and adolescents engaged in lab discussions about issues of conflict and guilt and rated mothers’ positive and negative communication during the tasks; observers rated these same behaviors. Adolescents also reported on their general internalizing symptoms prior to the discussions and feelings of guilt, shame, and experienced guilt induction following each discussion task. Structural equation models, parceling out shared and unique perceptions of maternal communication behaviors, showed that adolescents with more internalizing symptoms reported greater feelings of shame and perceived maternal guilt-induction following the discussion, and that these associations were mediated by adolescents’ unique perceptions of more maternal negativity. These findings highlight the potential role of cognitive biases in perpetuating established associations among adolescent internalizing symptoms, shame, and parental guilt-induction.