The patient was a 94-year-old male with a past medical history of hypertension, hyperlipidemia, iron deficiency anemia, chronic obstructive pulmonary disease, coronary artery disease status post four-vessel bypass, and tuberculosis status post right-sided total pneumonectomy. He presented to the emergency department with a 3-week history of dull/achy, nonradiating, mid-retrosternal chest pains which worsened with swallowing of solids associated with a 5-pound weight loss. On the morning of admission the patient ate a large meal and felt as though the food was lodged in his esophagus. This led to two episodes of nonbilious, nonbloody vomitus and recurrence of the chest pain. Upon admission, vitals revealed a temperature of 36.72 C, a pulse of 79 beats/min, a blood pressure of 157/69 mm Hg, a respiratory rate of 20/breaths/min, and an oxygen saturation of 93% on 2 L/min nasal cannula. Labs were remarkable for decreased hemoglobin of 10.1 g/dL, with a hematocrit of 29.4%, a mean corpuscular volume of 97.7, and a red blood cell distribution of 13.2%. Arterial blood gas was significant for PCO2 of 53.9 mm Hg, troponins were <0.05 ng/mL, and electrocardiography revealed normal sinus rhythm. A computed tomography scan of the chest did not reveal external compression of the esophagus, and thus an urgent esophagogastroduodenoscopy (EGD) was done to rule out food impaction. EGD revealed sloughing of esophageal mucosa with blueish discoloration of submucosal layer, dilated esophagus with decreased contraction, and erosive areas of ulceration (Fig. 1). Biopsies were taken in multiple regions of the esophagus. Pathological analysis demonstrated vacuolar degeneration at the midlevel of the epithelium with overlying hyperkeratosis and parakeratosis, with noted black/brown pigment present at the level of the split in the epithelium (Fig. 2). The patient was started on a full liquid diet and on this regimen reported resolution of odynophagia and chest pain. However, soon afterward, he developed acute on chronic hypoxic respiratory failure secondary to aspiration pneumonia as new left lower lung opacity was noted on chest X-ray. At this point the patient was made NPO, started on broad-spectrum antibiotics, placed on bilevel positive airway pressure, and admitted to the intensive care unit. He responded to treatment and was eventually weaned to nasal cannula. EGD was then repeated and showed a significant improvement in the esophageal mucosa and resolution of strictures and ulcerations (Fig. 3). At this point, the patient underwent a swallow evaluation and a modified barium swallow study, which were both negative. Following these results, he was placed on a soft diet which he tolerated well and was discharged home with gastrointestinal follow-up.