Congenital internal herniation is a rare condition presenting as recurrent abdominal pain or acute intestinal obstruction. In cases in which bowel incarceration or strangulation develop, rapid progression to bowel ischemia, necrosis or perforation is inevitable. Mortality in such cases has been reported to be as high as 50%. Despite advances in imaging modalities, arriving at a pre-operative diagnosis of a congenital internal herniation remains a challenge. We report such a case where imaging was unsuccessful in determining the cause of intestinal obstruction in a 3 year old child. Congenital internal herniation may result in disastrous consequences if not addressed in a timely fashion due to its rarity. Hence a high index of clinical suspicion is needed to avoid missing this diagnosis in a child presenting with recurrent abdominal pain or acute intestinal obstruction.