Pneumothorax is an abnormal collection of air between the lung and chest wall. Pneumothorax management guidelines put forth by the American College of Chest Physicians, European Respiratory Society, and British Thoracic Society are specific to adult patients. These guidelines' utility has not been addressed in pediatric populations, which causes significant management variation in younger patients. Additionally, pneumothorax management ranges from conservative to surgical treatment, but these approaches, timelines, and effectiveness have not been validated in significant numbers of pediatric patients. Here, we present three cases of pediatric pneumothorax with variable clinical courses-one with persistent air leak despite chest tube presence who underwent VATS and surgical resection of apical blebs. In contrast, the other two cases were managed more conservatively. We reviewed the current literature for diagnostic and management of pediatric patients with pneumothorax, which underscores the need for guidelines specific to this population.