Extubation is a crucial step in the weaning process of critically ill mechanically ventilated patients. Some patients may develop postextubation respiratory failure that may lead to the need for re-intubation, which is associated with increased morbidity and mortality. This review comprehensively explores postextubation respiratory support strategies, focusing on the efficacy of high-flow nasal cannula (HFNC) oxygen therapy and noninvasive ventilation (NIV) in reducing re-intubation rates among various patient populations. HFNC improves oxygenation and reduces the work of breathing. However, its effectiveness in preventing re-intubation varies according to the patient's characteristics and the predefined risk for re-intubation. NIV, alternatively, appears to provide substantial advantages in reducing the rates of re-intubation and respiratory failure, especially in patients with obesity and patients with hypercapnia. Therefore, the indiscriminate application of these support strategies without consideration of individual patient characteristics may not improve outcomes, highlighting the need for careful patient selection and tailored therapeutic strategies based on specific risk factors and clinical conditions. By aligning postextubation respiratory support strategies with patient-specific needs, we may improve the success rates of extubation, enhance overall recovery, and reduce the burden of reintubations in the intensive care setting.