Thoracic aortic dissection (TAD) with aorto-oesophageal fistula formation is an uncommon but fatal cause of haematemesis. A case is presented of a previously healthy 63-year-old man who presented to the emergency department with syncope and haematemesis. He had no history of heavy alcohol intake and was previously well. Bedside portable chest x ray revealed a widened mediastinum and, while awaiting a CT angiogram, he had a further large haematemesis which led to him undergoing resuscitation and rapid sequence intubation. CT angiography of his thoracic aorta revealed a large thoracic aortic aneurysm with dissection from the arch of the aorta down to the left iliac artery. The dissection had formed an aorto-oesophageal fistula in the proximal oesophagus. He was transferred to a tertiary referral centre for repair of the dissection and aorto-oesophageal fistula.