Unanticipated difficult airway still forms about 93% of the total number of difficult airway scenarios encountered. Difficult airway can be due to difficulty in mask ventilation, difficult laryngoscopy or difficulty in intubation. Difficult intubation can be due to a number of causes. Pathologies like enlarged lingual tonsil, valecular or epiglottic cysts, laryngeal papillomas, hyperplastic mucosal folds, oropharyngeal stenosis lead to difficulty visualizing the larynx. Tracheal stenosis, laryngeal webs, tumors of the larynx, airway trauma and undetected mediastinal masses lead to difficulty in advancing the endotracheal tube. Management of these cases is always challenging. Although a thorough history that includes previous endotracheal intubation, weight changes, episodes of dyspnea or wheeze may help identify at risk patients, very often these patients may be asymptomatic and the pathology may not be until the time of laryngoscopy and intubation. At the time of unanticipated crisis, following the stepwise protocol of difficult airway and being prepared for surgical airway access can prevent complications and save the life of the patient. Here we present two such cases of unanticipated difficult airway how we managed them. Post-operatively these patients were found to have laryngeal webs.