Most patients with serious illness prefer to die at home; however, for those requiring ongoing ventilatory support, this preference is often not honored due to the difficulties of arranging a palliative extubation at home. Here we present two cases of successful home palliative extubations, coordinated by a multidisciplinary team including critical care, palliative care, care management, hospice, and emergency medical services (EMS) clinicians. By exploring the operational and regulatory challenges accompanying these cases, we provide a road map for offering mechanically ventilated patients the choice of a death at home and provide truly holistic and patient-centered care.