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Background: Social anxiety is amongst the most prevalent adolescent mental health problems; however, it is often unrecognized due to its comorbidity with other anxiety problems such as generalized anxiety. Thus, understanding the unique developmental pathways to social anxiety is critical for improving its prevention. We examined the pathway from maternal shyness, when children were 4 years old, to adolescents' social anxiety at age 15 through social wariness at age 7. We hypothesized that childhood social wariness would mediate the association between maternal shyness and social anxiety in adolescence. Methods: Participants (N = 291; 54% female) were followed from early childhood to adolescence. Mothers reported on their own shyness when children were 4 years old. Social wariness toward unfamiliar peers was observed in the laboratory at ages 4 and 7. Adolescent social anxiety and generalized anxiety were assessed via self‐report, parent‐report, and clinical diagnoses at age 15. Results: Maternal shyness was positively associated with adolescent social anxiety but not generalized anxiety at age 15. Higher levels of maternal shyness at age 4 predicted greater social wariness at age 7, which in turn predicted greater social anxiety but not generalized anxiety at age 15. Social wariness at age 7 partially mediated the association between maternal shyness and adolescent social anxiety. Conclusions: This study identifies a unique developmental pathway from maternal shyness to adolescent social anxiety. Findings suggest that childhood social wariness connects maternal shyness to adolescent social anxiety. [ABSTRACT FROM AUTHOR]