Diaphragmatic hernia is a rare disorder in adolescents with oftentimes delayed diagnosis due to late-onset and non-specific clinical manifestations. In this report, we present a case of diaphragmatic hernia in an 18-year-old male, where initial diagnosis was complicated by confounding factors of type 1 diabetes mellitus and cannabinoid hyperemesis syndrome. This case highlights the importance of having a high index of suspicion for diaphragmatic hernia in patients with nonspecific gastrointestinal symptoms to ensure timely recognition and surgical intervention.