We describe a case of a very difficult intubation which was safely navigated through careful planning. Our patient presented initially with increasing hoarseness and shortness of breath over a 6-month period. This was investigated and the patient was found to have a large vocal cord mass and was referred for urgent microlaryngoscopy and vocal cord polypectomy. On the day of surgery the obstruction was noted and awake fiberoptic bronchoscopy was used with a remifentanil infusion. Given the mass was large and increased in size with expiration, the time frame to pass the tube was extremely short. We delivered a transtracheal injection of local anaesthesia. This approach allowed for safe passage of the endotracheal tube. In patients such as this it may be worth considering the use of a transtracheal injection in the first instance.