Occult enterorrhagia in infancy may become obscured and lead to diagnostic dilemma. Abnormal findings on investigative modalities, if not properly interpreted and clinically correlated, might complicate the matter leading to missed diagnosis and chronic anaemia. Occult enterorrhagia is an uncommon presentation of intestinal duplications. We describe the intriguing case of chronic anaemia in an infant, where concomitant endoscopic findings misled the diagnosis of jejunal duplication cyst as the cause of enterorrhagia.