Patients with respiratory failure due to obstructive lung disease present a challenge to the emergency physician. These patients have physiologic abnormalities that prevent adequate gas exchange and lung mechanics which render them at increased risk of cardiopulmonary decompensation when managed with invasive mechanical ventilation. This article addresses key principles when managing these challenging patients: patient-ventilator synchrony, air trapping and auto-positive end-expiratory pressure, and airway pressures. This article provides a practical workflow for the emergency physician responsible for managing these patients.