This case describes the difficulties faced in treating recurrent pleural effusions and diagnosing chylothorax in a preterm neonate. The mother of this case was one of the first neonates to undergo in utero pleural shunting for bilateral pleural effusions 30 years ago. She then presented with an antenatal diagnosis of fetal hydrops at 31+1 weeks gestation in her own pregnancy and her baby was delivered 3 days later due to concerns about fetal distress. The baby was clinically unstable with recurrent bilateral effusions which were extensively investigated and shown to be the result of congenital chylothorax of possible genetic origin. This case demonstrates the challenges of managing chylothorax in the newborn.