Tracheal extubation in both the critical care and anesthesia setting is not only an important milestone for patient recovery, but also a procedure that carries a considerable risk of complication or failure. Mechanical ventilation is associated with significant complications that are time-dependent in nature, with a longer duration of intubation resulting in a higher incidence of complications, including ventilator-associated pneumonia, and increased mortality. Extubation failure and subsequent re-intubation are associated with an overall increase in the duration of mechanical ventilation, increased mortality, a greater need for tracheostomy, and higher medical costs. These risks demand that the process of extubation be managed by practitioners with a detailed understanding of the causes of extubation failure and the potential complications. A pre-established extubation plan with considerations made for the possible need for re-intubation is of the utmost importance.