Abstract Pneumothorax is a life-threatening condition with potential iatrogenic causes which can extend to pneumomediastinum and pneumoperitoneum. Risk factors of spontaneous pneumothorax include prematurity, low birthweight, low APGAR scores and caesarean-section delivery. A 1255 grams preterm boy (Twin-2) was born at 28+3 weeks of gestation by emergency lower segment caesarean section. He showed signs of respiratory distress after uncomplicated endotracheal tube insertion which was required due to apnoeic episodes during continuous positive airway pressure ventilation. Recurring tube thoracocentesis and high frequency oscillatory ventilation (HFOV) treated persistent right-sided pneumothorax and nonsurgical pneumoperitoneum, with improvement on day-10, gradual removal of five chest drains by day-19 and extubation on day-24. Transillumination and chest radiography were main diagnostic investigations. Laryngotracheobronchoscopy on day-16 identified erythema and possible old injury at the carina. He was also treated for hypotension, suspected sepsis and pulmonary hypertension and was discharged home on day-66. Identifying pneumothorax promptly is essential to reduce morbidity and mortality. Lung ultrasound would improve diagnosis and monitoring. Management is patient-specific and includes needle and tube thoracocentesis and HFOV. Use of blood patch, fibrin glue or chemical agents, selective bronchial ventilation have been reported. Surgery is usually applied in unstable patients where bridging the defect is not feasible. nonsurgical pneumoperitoneum should be considered in ventilated neonates and those with airway injury to avoid exploratory laparotomy. Our case demonstrates challenges of managing a massive air leak in a premature newborn, who with adequate tube thoracocentesis and HFOV, successfully recovered from presumed iatrogenic persistent pneumothorax and pneumoperitoneum with conservative management.