Nutritional support is essential for critically ill patients to reduce mortality and length of stay. Frequently nasogastric (NG) tubes are used to provide enteral nutrition. A very rare risk of NG tube placement is esophageal perforation, most commonly in the thoracic portion of the esophagus. Here we describe a case of a 41-year-old male with multiple risk factors for esophageal integrity disruption who initially presented for diabetic ketoacidosis (DKA) requiring intubation. Following intubation, an NG tube was placed for nutritional support. The following day the patient developed hydropneumothorax and hydropneumoperitoneum. He was taken emergently for surgical correction of suspected perforation. It was found that the patient had esophageal perforation from the distal esophagus to the proximal portion of the lesser curvature of the stomach. The NG tube transversed the proximal portion of the tear and re-entered at a distal site. The distal portions of the esophagus showed necrotic superficial layers with viable muscularis layers. The patient gradually improved after surgical intervention and was discharged to a long-term acute care facility. It is essential as medical providers to be familiar with complications of NG tube placement and risk factors that could increase the risk of esophageal perforation.