Bronchoscopic-guided percutaneous dilational tracheostomy has become one of the most common elective tracheostomy methods for patients requiring prolonged ventilatory support. The safety profile, patient selection, and risks as well as complication management, when compared with an open surgical technique, remain somewhat controversial with no clear recommendations. We present a case of a critically ill patient undergoing percutaneous dilation tracheostomy complicated by tracheal wall injury and airway loss. The airway was successfully conservatively managed as well as the tracheal injury. Anesthetic implications, safety, and management options as well as recommendations are reviewed.