Retention of an intercostal drain segment is an uncommon and infrequently reported complication of underwater seal drain use. We report the case of a 66-year-old New Zealand European male who underwent bilateral lung transplantation for severe chronic obstructive pulmonary disease and bronchiectasis. The patient required a return to the operating room for exploratory surgery after an intercostal drain severed during its attempted removal and became retained within the chest cavity. A deep suture had inadvertently been passed around the chest drain intraoperatively. In the event of such a complication, prompt recognition and removal of the retained segment is required. This novel case is reported to highlight the possibility of an entrapped suture as a cause of resistance when attempting to remove an intercostal drain. Kinking on a chest X-ray may also point to this problem, and senior input should be sought early if radiographic findings are coupled with clinical difficulties.