A 28-year old man required invasive mechanical ventilation in view of organophosphorus poisoning in a peripheral hospital. His trachea was extubated ten days later following which he presented with dysphagia, voice change, burping, fever and cough. He was referred to our hospital for further management. His barium swallow radiograph showed a large tracheo-oesophageal fistula. Therefore, he was scheduled for oesophageal transection and colonic transposition. Following induction of anaesthesia, despite easy laryngoscopy view (Cormack Lehane grade 1), the tracheal intubation was found to be difficult as the tube tended to pass through the fistula into the oesophagus repeatedly as confirmed by absence of capnogram trace. Attempts to bypass the fistula using a fibreoptic scope and even a double lumen tube also failed. Identification of oesophageal intubation would have been missed or possibly detected late in this case with disastrous consequences but for absence of capnogram. Finally, the tracheal tube was successfully negotiated beyond the fistula with the help of a gum elastic bougie directed anteriorly into the trachea and a good capnogram was obtained. The surgery was uneventful and the trachea was extubated 24 h later in the intensive care unit following which the patient developed stridor requiring permanent tracheostomy. This case report illustrates the novel use for gum elastic bougie during tracheal intubation. This also highlights the importance of repeated measurement of tracheal cuff pressure in patients especially those receiving long duration mechanical ventilation.