We report the case of an 80-year-old man who developed a colocutaneous fistula as a complication of anastomotic leakage following segmental colonic resection. The patient presented with an abscess of the abdominal wall, subcutaneous emphysema, pneumomediastinum, pneumothorax, pneumorrhachis, and pneumoscrotum. We discuss the possible mechanisms for these unusual clinical presentations of extraperitoneal air following anastomotic leak.