Pneumonia is a common clinical problem treated by numerous specialists. However, when a patient cannot breathe properly while lying flat, other etiologies must be explored. When a patient is then found to have systolic heart failure with an ejection fraction of less than 15%, significant concern is raised when discharging the patient after they become hemodynamically stable. A likely fatal culprit that a patient could face would be an arrhythmia. To prevent death due to fatal arrhythmias in the setting of heart failure, patients are trialed on a wearable defibrillator, the LifeVest, to determine whether they will need an implantable cardioverter-defibrillator (ICD). We present the case of a patient who was diagnosed with systolic heart failure when his complications arising from pneumonia did not correlate with his symptoms. During his trial of the LifeVest, his life was saved by defibrillation. He was then successfully brought to the hospital for placement of a permanent implantable cardioverter-defibrillator (ICD).