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Intraoperative tracheobronchial injury is an uncommon but potentially life-threatening complication during thoracic surgery. We present two cases: one female patient in her 70s and another female patient in her 40s scheduled for robotic right upper and lower lobectomy respectively. Both cases were complicated by iatrogenic injuries to the left mainstem bronchus requiring repair. Successful management of the unanticipated iatrogenic injuries required ongoing communication and coordination between the anaesthesiologist and surgeon and a shift in ventilation strategies to adapt to surgical conditions and allow repair while maintaining a closed chest approach.