Introduction: Primary spontaneous pneumothorax (PSP) predominantly affects young adult males; however, the overall incidence in adolescents appears to be increasing. Unfortunately, impactful literature investigating the adolescent patient population is limited. This chapter aims to identify recent and targeted data to provide cohesive recommendations for pediatric surgeons. Methods: PubMed was queried using a systematic search methodology to identify existing studies, published between January 1, 2012—December 31, 2022, that investigated initial management approaches to PSP and related clinical outcomes such as success of non-operative management, hospital length of stay, recurrence rates, and cost. Results: Stable children and adolescents presenting with their first episode of PSP can undergo an initial trial of observation, regardless of initial pneumothorax size. A trial of aspiration with small-bore thoracostomy should be employed initially to alleviate more severe presenting symptoms or to differentiate ongoing air leak from a sealed bleb. Patients who fail observation with exacerbation of symptoms or enlarging pneumothorax, or those who fail an aspiration test, would benefit from early VATS as it leads to reduction in hospital length of stay and recurrence when compared to chest tube drainage alone. Conclusion: These results indicate shifting practice patterns for treatment of PSP in pediatrics with targeted identification of patients likely to fail conservative management. An initial observation period can differentiate patients who have sealed a ruptured parenchymal bleb from those with an ongoing air leak, which should prompt early progression to definitive surgical intervention. Additionally, there remains a role for aspiration for diagnostic benefit and symptom control.