A patient presented with dyspnea following an upper GI endoscopy. Imaging found pneumomediastinum, subcutaneous emphysema, a right pleural effusion, and free intraperitoneal air. This was diagnosed as an iatrogenic esophageal perforation during the endoscopy, with defects in the upper third of the esophagus wall allowing air to dissect into the mediastinum and peritoneum. A non-ionic contrast would be used instead of barium for follow-up exams due to risk of mediastinal fibrosis from the perforation.