Pigtail catheters have emerged as an effective and less morbid alternative to traditional chest tubes for evacuation of pleural air. Rare complications in the literature have been reported. We report a case of a 92-year-old male who presented with dyspnea and shock, noted to have a pneumothorax requiring tube thoracostomy. Computed tomography demonstrated pigtail within the lung parenchyma. We discuss the implications of this occurrence.