A 64-year-old, cachectic man with body mass index (BMI) <19 visited in clinic with the chief complaint of dysphagia for 6 months. He reported a 2-year history of reflux and heartburn, for which he has been taking pantoprazole but reported only 40% relief of reflux symptoms. He reported progressive solid food mid-chest dysphagia. Additional comorbidities included severe pulmonary bronchiectasis and bullous emphysema and a history of treated pulmonary tuberculosis 40 years prior and two previous episodes of spontaneous pneumothorax in the right-sided lung treated with a chest tube. A chest X-ray showed a calcified aorta crossing the midline (Figure 1). A CT scan done for assessment of pneumothorax showed a torturous descending thoracic aorta and a dilated mid-/proximal esophagus. The diameter of the descending aorta was 41 mm, and it crossed the midline. For evaluation of dysphagia, a barium swallow was performed, which showed a narrowing in the mid-esophagus with proximal dilation and lack of peristalsis (Figure 2). Upper gastrointestinal endoscopy showed a dilated esophagus with eccentric extraluminal compression. High-resolution manometry (HRM) showed an absence of peristalsis and a vascular pressure artifact around the mid-esophagus correlating with the external aortic compression (Figure 3). Due to alarming weight loss and a BMI <19, we recommended a feeding jejunostomy to maintain nutrition before scheduling definitive treatment.