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Extubation failure is associated with a poor prognosis, but the respective roles for reintubation per se and underlying disease severity remain unclear. Our objectives were to evaluate the impact of failed extubation, whether planned or unplanned, on patient outcomes and to identify a patient subset at risk for extubation failure.Prospective 1-yr observational study with daily data collection.Thirteen-bed medical intensive care unit in a teaching hospital.Consecutive patients requiring invasive mechanical ventilation were screened and followed until discharge or death.None.Of 168 planned extubations in 340 patients, 26 (15%) failed. Of these 26 patients, seven (27%) had pneumonia and 13 (50%) died after reintubation. Compared with successfully extubated patients, the patients with failed extubation were not significantly different regarding disease severity, mechanical ventilation duration, or blood gas values. Age and underlying diseases were the only factors associated with extubation failure, and extubation failure occurred in 34% of patients >65 yrs with chronic cardiac or respiratory disease compared with only 9% of other patients (p < .01). Unplanned extubation occurred in 9% of patients, and inadequate endotracheal tube position was a risk factor. Failure of both planned and unplanned extubation was specifically associated with significant rapid worsening of daily organ dysfunction scores.Patients >65 yrs with underlying chronic cardiac or respiratory disease are at high risk for extubation failure and subsequent pneumonia and death. Contrasting with successful extubation, failed planned or unplanned extubation was followed by marked clinical deterioration, suggesting a direct and specific effect of extubation failure and reintubation on patient outcomes.