Patients with head and neck cancer are at an increased risk of airway complications, not only because of the tumor itself and the need for a shared airway, but also the treatment of cancer (including surgery, radiotherapy, and chemotherapy) poses major challenges in airway management. The perioperative assessment, therefore, needs to be comprehensive to allow us to predict possible airway difficulty. Moreover, the suitability and feasibility of primary and rescue plans are needed to be assessed for each individual patient. In this case report, we describe a case of a patient, with recurrent tongue cancer with prior history of surgery and radiotherapy to the head and neck region. The difficulty in managing the airway in this case was anticipated correctly and subsequently encountered in almost every step, including bag-mask ventilation, video-laryngoscopy, and laryngeal mask airway (LMA) insertion in a patient. Despite the presence of visual aids and algorithms for the management of a difficult airway, a premeditated airway management plan, and the availability of all necessary equipment and expertise, a break in structure and sequence was encountered, which was quickly corrected and saved the patient from any harm.