Maxillofacial surgeries can present unique anesthetic challenges due to potentially complex anatomy and the close proximity of the patient's airway to the surgical field. Damage to the tracheal tube (TT) during maxillofacial surgery may lead to significant airway compromise. We report the management of a patient with a partially severed TT during Le Fort surgery for midfacial hypoplasia and management strategies based on peer-reviewed literature. This case illustrates the clinical clues associated with a damaged TT and explores the challenges of managing this potentially catastrophic issue.