Aorto-oesophageal fistula is a life threatening condition in which there is an abnormal connection between the aorta and oesophagus, and is a rare complication of foreign body ingestion from which few patients survive. Classic presentation is with Chiari’s triad of mid thoracic pain, sentinel arterial haemorrhage and massive exsanguination after a symptom free interval. A 36-year-old male was transferred to a tertiary care hospital with a history of epigastric pain and discomfort in his retro-sternal area. According to the history, he had ingested fish the previous day while consuming alcohol. He was treated for four days in the hospital, and discharged with a diagnosis of alcohol induced gastritis. He was re-admitted later the same day with an episode of haematemesis. However, investigations such as chest radiography and oesophagogastroduodenoscopy were not carried out. He developed massive haematemesis 12 hours later, and despite vigorous resuscitation and emergency surgery, he expired. Autopsy revealed an impacted fish bone at the junction of upper and middle third of the oesophagus creating a fistula tract from oesophagus to thoracic aorta which resulted in exsanguination, haemorrhagic shock and death. Even though mortality is very high, survival is possible with a high index of suspicion, early diagnosis and rapid surgical intervention. Autopsy findings, review of the literature and medico-legal aspects of possible medical negligence are discussed.