Aorto-oesophageal fistula (AEF) is rare and fatal without intervention. Having consumed a date pit 2 weeks prior, the patient in this case presented with the 'Chiari' triad of chest pain, sentinel arterial upper gastro-intestinal haemorrhage and exsanguination after an asymptomatic interval. Following resuscitation, the patient was managed with a Blakemore tube with both oesophageal and gastric balloons inflated to systemic pressures. An aortic stent graft was planned but the patient died on the operating table. AEFs can be treated surgically with either open or endovascular repair. Open repair is highly risky and involves combined replacement/bypass of the thoracic aorta along with resection/repair of the involved oesophagus. Endovascular repair can prevent fatal exsanguination and increase the likelihood of survival but is associated with a significant rate of secondary infection, recurrence of fistula, mediastinitis and sepsis. Further studies are required to inform on management.