Aortoesophageal fistulas are uncommon, dreadful vascular events, most frequently found in the setting of thoracic aorta aneurysms. Patients usually present with thoracic pain, dysphagia and sentinel hematemesis - the Chiari triad - followed by life threatening hematemesis. Emergent open surgery with debridement of necrotic tissue and in situ aortic graft repair is currently the best strategy. However, in patients which cannot withstand surgery, endovascular repair is currently gaining acceptance as a palliative treatment or as a bridge to surgery. We present a case of a 55-year-old female with a past of heavy alcohol abuse and a previously unknown massive aortic aneurysm, who presented to the emergency department complai- ning of acute dysphagia and epigastric pain. An abdominal ultrasound revealed left pleural effusion and suspected clots in the pleural space. A thoracic CTA was promptly done, where a spontaneous ruptured aortic aneurysm with aortoesophageal fistula was discovered. The team, fearing open surgery due to poor cardiac function, opted for a thoracic endovascular aortic repair. The aortoesophageal fistula dissected the esophageal wall in all of its thickness without rupture into the lumen. This was complicated with esophageal ischemia, aneurysmal sac infection and mediastinitis. Because the patient was in shock, in order to help control the infection, an esophageal prosthesis was placed, followed by proximal esophagostomy, distal esophageal closure and gastrostomy. Six months after initial presentation, the patient died at the emergency room, shortly after reentering with massive hematemesis and hypovolemic shock of undetermined origin.