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Respiratory complications after tracheal extubation are associated with significant morbidity and mortality, suggesting that process improvements in this clinical area are needed. The decreased rate of respiratory adverse events occurring during tracheal intubation since the implementation of guidelines for difficult airway management supports the value of education and guidelines in advancing clinical practice. Accurate use of terms in defining concepts and describing distinct clinical conditions is paramount to facilitating understanding and fostering education in the treatment of tracheal extubation-related complications. As an example, understanding the distinction between extubation failure and weaning failure allows one to appreciate the need for pre-extubation tests that focus on assessing airway patency in addition to evaluating the ability to breathe spontaneously. Tracheal reintubation after planned extubation is a relatively rare event in the postoperative period of elective surgeries, with reported rates of reintubation in the operating room and postanesthesia care unit between 0.1% and 0.45%, but is a fairly common event in critically ill patients (0.4%–25%). Conditions such as obesity, obstructive sleep apnea, major head/neck and upper airway surgery, and obstetric and cervical spine procedures carry significantly increased risks of extubation failure and are frequently associated with difficult airway management. Extubation failure follows loss of upper airway patency. Edema, soft tissue collapse, and laryngospasm are among the most frequent mechanisms of upper airway obstruction. Planning for tracheal extubation is a critical component of a successful airway management strategy, particularly when dealing with situations at increased risk for extubation failure and in patients with difficult airways. Adequate planning requires identification of patients who have or may develop a difficult airway, recognition of situations at increased risk of postextubation airway compromise, and understanding the causes and underlying mechanisms of extubation failure. An effective strategy to minimize postextubation airway complications should include preemptive optimization of patients’ conditions, careful timing of extubation, the presence of experienced personnel trained in advanced airway management, and the availability of the necessary equipment and appropriate postextubation monitoring.