Paratracheal air cyst encompasses conditions including tracheoceles, bronchogenic cysts, lymphoepithelial cysts, and tracheal diverticula. The occurrence of tracheal diverticulum is rare and usually does not manifest clinically or may cause symptoms like chronic cough. However, it may have a rare presentation—like in our case—where rupture of tracheal diverticulum post-intubation and assisted ventilation for elective surgery led to pneumothorax, pneumopericardium, pneumomediastinum, pneumoperitoneum, and pneumoretroperitoneum. It may pose diagnostic dilemmas in such cases. An understanding of the underlying mechanism helps in the management, which in majority of cases is conservative.