Nasogastric tube insertion (NGT) is a common bedside procedure and malpositioned tubes into the tracheobronchial are not uncommon. These can be associated with pulmonary complications. Significantly, pneumothoraces are rare but potential complications that clinicians need to be aware of. We herein report a case of pneumothorax following NGT insertion that necessitated operative management. A 72-year-old male smoker was undergoing rehabilitation after a recent cerebrovascular accident. A NGT change was done and the chest radiograph done to check placement demonstrated the NGT in the right bronchus with the tip in the right pleural space. The NGT was removed and a new one reinserted. A repeat chest radiograph demonstrated a right sided pneumothorax. He underwent radiologically guided chest drain insertion and subsequently required thoracoscopic surgery where a wedge resection of the right lower lobe was performed. The chest drain was removed on day two post operatively and he made an uneventful recovery.