Prosocial behavior is a multifaceted construct that may be expressed and received in a myriad of ways, thereby posing several challenges in measurement. Undoubtedly, significant advancements in the measurement of prosocial behavior have been made since the construct first found its way onto the research stage; however, a few fundamental problems persist with regard to: 1) the absence of a universally employed definition, 2) substantial variation in operationalization and measurement of the construct, and 3) inconsistent reports regarding the nature of prosocial development during the transition between adolescence and young adulthood. These issues are further compounded under conditions of adversity or in consideration of cultural influence. Researchers often face challenges conceptualizing and developing standardized metrics of prosocial behavior that are representative of adolescent experiences across cultures. The overarching aim of this multiphase mixed methods investigation was to place the construct under scrutiny, examining both measurement and conceptual equivalence across diverse youth.