With adolescence being a period for potential challenges but also positive growth, courage can aid adolescents in rising to some of these challenges. Yet few studies have investigated predictors and mechanisms of courage. The present study examined how three parenting constructs (attachment, autonomy support, and helicopter parenting) predict courage and if self-esteem or emotion regulation serve as mediators. The present study assessed predictors at Time 1 and courage at one-year follow-up. The sample included 203 American adolescents (51.7% girls, 14-15 year olds). Results suggested that relations between several parental variables (anxious attachment to parents, avoidant attachment to fathers, autonomy support of parents) and adolescent courage were mediated by self-esteem. In addition, cognitive reappraisal mediated associations between two mother-related variables (avoidant attachment, helicopter parenting) and courage. Findings contribute to the limited empirical research on adolescents' development of courage.