Background: This case highlights challenges in the assessment and management of the “difficult airway” patient in the SARS-CoV-2 (COVID-19) pandemic era. Methods: A 60-year-old male with history of recent TORS resection, free flap reconstruction and tracheostomy for p16+ squamous cell carcinoma presented with stridor and dyspnea one month after decannulation. Careful planning by a multidisciplinary team allowed for appropriate staffing and personal protective equipment, preparations for emergency airway management, evaluation via nasopharyngolaryngoscopy, and COVID testing. The patient was found to be COVID negative and underwent imaging which revealed new pulmonary nodules and a tracheal lesion. Results: The patient was safely transorally intubated in the operating room. The tracheal lesion was removed endoscopically and tracheostomy was avoided. Conclusions: This case highlights the importance of careful and collaborative decision making for the management of head and neck cancer and other “difficult airway” patients during the COVID-19 epidemic.