The chapter explores how children’s and YA fiction’s repurposing of fairy-tale tropes serves a non-didactic, educative, therapeutic agenda to foster young readers’ fantasizing agency resulting in social skills of resilience and solidarity. An imaginative construction of non-existent but possible worlds allows for a playful mockery of normative thinking and disciplinary ideology. It also holds ethical responsibilities and opens up political vistas by urging the empathic consideration of others’ perspectives and the recognition of communal storytelling’s role in shaping our understanding of past, present, and future. Fairy tales’ core patterns of trauma, quest, and remedy overlap with common themes of YA problem novels and hence help young readers on their journeys of self-discovery to cope with their own vulnerabilities, uncontrollable aspects of reality, and new monsters of postmillennial times. The leitmotif on the adolescent struggle for the acceptance of difference—crossing the boundaries to recognize who you are—resonates particularly well with the twisted versions of classic fairy tales that subversively rewrite canonized master narratives. The study of fairy-tale cultures inoculated into children’s/YA literatures reveals the changing meanings attributed to fantasy, along with the different modes of dis/enchantment elicited by media transition.