Extubation is a critical yet often overlooked aspect of airway management. Although frequently performed in anaesthetic practice, extubation can be a complex and challenging event that remains under-represented in clinical teaching. This report describes the case of a 41-year-old male patient who sustained facial and chest trauma following a pedestrian motor vehicle accident. He underwent open reduction and internal fixation of a mandibular fracture. Despite an uneventful induction with nasal intubation and intraoperative course, he experienced two episodes of extubation failure in theatre, both associated with hypoxia and hypercapnia, requiring urgent reintubation. Contributing factors included maxillofacial trauma, chest trauma, and likely airway oedema. Ultimately, he could not be safely extubated in theatre and was admitted intubated to an intensive care unit (ICU). This case highlights the importance of structured, proactive planning for extubation in high-risk patients. It underscores the need for thorough risk stratification, anticipation of complications, and readiness to intervene in the event of extubation failure. It also draws attention to the need for greater emphasis on extubation management in anaesthetic training, as well as the potential role for validated tools to predict extubation risk.