Duplication cysts are rare congenital malformations that can present with a variety of symptoms that may change during the course of an acute admission. We report a case in which a four-year-old boy presented with signs of small bowel obstruction that following imaging were found to be secondary to bowel compression by a large duplication cyst. The symptoms changed when the cyst ruptured. We highlight the importance of ultrasound in establishing the diagnosis of enteric duplication cysts in the symptomatic paediatric population. We also explore the differential diagnosis and complications that can be caused by these congenital anomalies.