Nasogastric (NG) tube misplacement into the airways is a rare complication. The presence of a cuffed endotracheal or tracheostomic tube often gives primary care providers a false sense of security. This report presents a case of inadvertent NG tube insertion into the right lower lobe bronchus of a 79-year-old patient with advanced chronic obstructive pulmonary disease, resulting in pneumonia and septic shock. In this report, the literature is reviewed, the influence of tube size on complications is compared, and the reliability of different methods to verify correct tube position is discussed. We conclude that a cuffed tracheostomic tube does not prevent advancement of a large-bore feeding tube into the tracheobronchial system. If any doubt exists regarding proper tube position, a chest radiograph should be obtained prior to initiation of feeding.