Behavioral inhibition (BI) and maternal over-control are early risk factors for later childhood internalizing problems, particularly social anxiety disorder (SAD). Consistently high BI across childhood appears to confer risk for the onset of SAD by adolescence. However, no prior studies have prospectively examined observed maternal over-control as a risk factor for adolescent social anxiety (SA) among children initially selected for BI. The present prospective longitudinal study examines the direct and indirect relations between these early risk factors and adolescent SA symptoms and SAD, using a multi-method approach. The sample consisted of 176 participants initially recruited as infants and assessed for temperamental reactivity to novel stimuli at age 4 months. BI was measured via observations and parent-report across multiple assessments between the ages of 14 months and 7 years. Maternal over-control was assessed observationally during parent-child interaction tasks at 7 years. Adolescents (ages 14-17 years) and parents provided independent reports of adolescent SA symptoms. Results indicated that higher maternal over-control at 7 years predicted higher SA symptoms and lifetime rates of SAD during adolescence. Additionally, there was a significant interaction between consistently high BI and maternal over-control, such that patterns of consistently high BI predicted higher adolescent SA symptoms in the presence of high maternal over-control. High BI across childhood was not significantly associated with adolescent SA symptoms when children experienced low maternal over-control. These findings have the potential to inform prevention and early intervention programs by identifying particularly at-risk youth and specific targets of treatment.