Iatrogenic tracheobronchial injury is rare. Limited data is available on such injuries in infants and management of these is challenging. We present a 7-month-old male infant who was diagnosed with oesophageal stricture, and was planned for thoracoscopic repair of the same. Anaesthetic management with a single lumen tracheal tube ensued. However, an intraoperative loss of capnogram and desaturation led to the diagnosis of iatrogenic tracheobronchial injury. After unsuccessful pursuits with a Fogarty catheter through the tracheobronchial tear and through the right bronchus for lung isolation, blind left endobronchial intubation with a smaller tube and one lung ventilation was successful. The rent was repaired by an open procedure, and oesophageal surgery completed. However, the child succumbed and died of multiorgan failure 3 days later.