A 72-year-old woman presented to the hospital with a 2-day history of dyspnea. Left maxillary sinus cancer had been diagnosed 10 years earlier and treated with left orbital exenteration, maxillectomy, and radiation complicated by trismus. She was diagnosed with community-acquired pneumonia and admitted for antibiotic therapy. During the middle of the night on hospital Day 2, a rapid response was called in the setting of respiratory distress and critical hypoxia, presumed to be due to progressive worsening of her severe pneumonia. During airway evaluation, the patient’s mouth was unable to be opened owing to her underlying trismus. As an alternative to an emergent tracheostomy, orbital intubation was attempted after visualizing the larynx through her left orbit. A stat portable plain film confirmed successful endotracheal intubation, and the patient was extubated in 48 hours and discharged from the hospital in stable condition after 5 days.