We describe a rare case of aorto-oesophageal fistula and aortic pseudoaneurysm in a middle-aged man, who presented with chest pain and haematemesis 1 week after swallowing a fish bone. Oesophagogastroduodenoscopy and computed tomographic angiography findings were consistent with oesophageal perforation, proximal descending aortic pseudoaneurysm, and aorto-oesophageal fistula. Thoracic endovascular aortic repair was performed. The patient died from severe mediastinal sepsis. Early surgical intervention and broad-spectrum antibiotic therapy are crucial in preventing life-threatening mediastinal infection.