Subcutaneous emphysema is defined by air becoming confined in the soft tissues beneath the skin and it may occur following various surgical procedures and specific penetrating trauma. While treatment is typically conservative and not required in most cases, massive subcutaneous emphysema may cause significant morbidity and sometimes life-threatening complications such as tension pneumomediastinum and respiratory compromise. Notably, no instances of self-inflicted air insufflation into the abdominal cavity have been reported in the literature. This report depicts a case of a self-inflicted air insufflation in a 40-year-old man via penetration of his umbilicus with a manual air compressor leading to widespread subcutaneous emphysema, pneumoperitoneum, pneumomediastinum, pneumopericardium, and pneumothorax. The pathway of possible air movement between body cavities has been theorized, but excluding case reports and anecdotal evidence, treatment of severe subcutaneous emphysema is less clear. This case report intends to record this unique instance of extensive subcutaneous emphysema and to emphasize the necessity for more definitive guidelines in managing these patients.