Background: A large theoretical and empirical literature indicates that parenting practices affect young people’s well-being and resilience, but there is much still to learn about psychological mechanisms, especially beyond infancy/early childhood. A recent model of authentic self-esteem argues that it arises out of experiences of challenge situations shared with parents and that it can subsequently act as a protective factor that supports well-being and resilience among young people. The aim of the current study is to test (a) if parenting about challenges can predict 3 indices of adolescents’ well-being, namely their social anxiety, disrupted classroom concentration, and ability to spontaneously generate resilient strategies; and more substantially, (b) if authentic self-esteem can mediate those associations if found. Method: Adolescents (N = 836) completed a questionnaire that measured all the study variables via self-report with the exception that unprompted open questions were used to gauge their ability to spontaneously generate resilient strategies. Results: Parental discussions of challenges did significantly predict all 3 well-being indices, and authentic self-esteem was found to mediate all these relationships. Discussion: These results support the view that parenting about challenges is a practice that supports well-being and resilience in adolescents. It appears to do so through promoting the development of authentic self-esteem, a capacity to evaluate the self in a positive manner in the context of challenges. The theoretical and practical significance of these findings are discussed. (PsycInfo Database Record (c) 2022 APA, all rights reserved)