Tracheopulmonary complications following placement of a nasogastric (NG) feeding tube are uncommon but can cause significant morbidity and mortality. In this case report, an 83-year-old woman of American Society of Anesthesiologists class IV with underlying pulmonary disease required placement of an NG feeding tube after surgical treatment of primary squamous cell carcinoma of the tongue. Malpositioning of the NG feeding tube into the right pleural space was confirmed by computed tomography. Removal of the NG feeding tube resulted in a tension pneumothorax that necessitated chest tube placement. Because of the difficulty of blind NG feeding tube placement in this patient, the subsequently placed NG feeding tube was successfully positioned with the aid of a video laryngoscope. This case report illustrates the risk of NG feeding tube malpositioning in a nasally intubated patient undergoing head and neck surgery and discusses improvements in techniques for proper NG feeding tube placement.