A 49-year-old gentleman presented with epigastric pain for one day associated with one episode of vomiting and dyspnoea. Respiratory examination showed reduced breath sound over his left lower zone. He was treated as left spontaneous pneumothorax and left lung empyema requiring left chest tube insertion and intravenous antibiotics. His left pleural fluid biochemistry result was exudative while its centrifuge showed empyema. In ward, we noticed food material draining from his left chest tube during feeding. An urgent contrast enhanced computed tomography (CECT) thorax showed a left oesophageal-pleural fistula with possible broncho-oesophageal fistula. During oesoph- agogastroduodenoscopy (OGDS), air bubbles were seen in his left under-water chest drainage during air-insufflation of the oesophagus. The revised diagnosis was Boerhaave syndrome. He was treated with an esophageal stent to cover the perforation and a left lung decortication via video assisted thoracoscopic surgery (VATS) for his left empyema. He improved and was discharged well.