Intubation in patients with an obstruction of the glottis due to a large mass may present great challenge to most anesthesiologists. If tracheostomy is not available, flexible fiberscope guided endotracheal intubation is now the part of the standard management in these cases, but difficulty in advancing the tracheal tube over the fiberscope and into the trachea may be encountered. In this case, a 60-year-old male with a huge supraglottic mass was given general anesthesia for laryngomicroscopic surgery and debulking of the mass lesion. We planned an awake flexible fiberoptic intubation but failed to railroad the tube over the fiberscope even after successfully placing the scope inside the trachea. During various attempts to pass the tracheal entrance, the patient coughed and the tube slid into the trachea as mass moved aside and we could successfully secure the airway.