An 86-year-old man with a history of dementia presented to an emergency department with 2 weeks of worsening nausea and vomiting. His vomiting became “violent” and was associated with chest pain and shortness of breath 1 hour before presentation. A computed tomographic (CT) scan of his chest showed pneumomediastinum (image A, arrow). He was endotracheally intubated and treated with a fentanyl infusion titrated to comfort, piperacillin/tazobactam, and intravenous fluids. A water-soluble contrast swallow study obtained by repositioning his orogastric tube into his esophagus demonstrated contrast extravasation from the distal esophagus into the mediastinum consistent with a perforation (image B, arrow). Because of concerns about quality of life if he were to survive this critical illness, surgical repair was not done. The patient was extubated and provided with comfort care and died soon after presentation.