The diagnosis of appendicitis is challenging in neonates and infants due to the unspecific clinical signs and symptoms, presence of many differentials and inability to elicit history from a preverbal child. Gangrenous retrocolic appendix mimicking incarcerated umbilical hernia is rare. Consequently, the correct diagnosis of a gangrenous retrocolic appendix in a 13-month-old boy who presented with features highly suggestive of incarceration of proboscoid congenital umbilical hernia was very challenging. This case is presented to highlight the diagnostic challenge and increase the suspicion of appendicitis in infants with non-classical clinical features. (Source: Journal of Tropical Pediatrics)