Background: Airway stenosis is a known complication of prolonged intubation in hospitalized patients. With the high rate of intubations in patients with COVID-19 pneumonia, laryngotracheal stenosis (LTS) is a complication of COVID-19 that drastically reduces quality of life for patients who may remain tracheostomy-dependent. Methods: Patient medical history, laryngoscopy, and CT imaging were obtained from medical records. Results: We report four cases of complicated LTS following intubation after COVID-19 pneumonia and explore the current literature in a narrative review. Four patients developed LTS following intubation from COVID-19 pneumonia. Three patients remain tracheostomy-dependent, and the fourth required a heroic operative schedule to avoid tracheostomy. Conclusion: Intubation for COVID-19 pneumonia can result in severe LTS, which may persist despite endoscopic intervention.