Iatrogenic esophageal perforation in neonates, though rare, is a serious condition with high mortality. It is almost exclusively secondary to invasive instrumentation complications in intensive care settings. Forceful or repeated orogastric (OG) or nasogastric (NG) tube insertion, vigorous suctioning to clear the airway, and trauma during airway intubation are the leading causes. Being rare in occurrence, a high index of suspicion should be maintained for early diagnosis and prompt treatment to prevent mortality. We present a similar case in a 2.6 kg male neonate who developed this complication from OG tube placement in the neonatal intensive care unit during the treatment of respiratory distress and parapneumonic effusion.