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Congenital Diaphragmatic Hernia (CDH) is due to a defect in the diaphragm and is usually detected soon after birth. However, in rare cases, asymptomatic CDHs can be missed and present later in life. Late-presentation CDH can be misdiagnosed as tension pneumothorax leading to iatrogenic complications. We report a case of a 10-year-old boy who presented with non-specific symptoms of vomiting and occasional breathlessness, but was subsequently diagnosed as late-presentation CDH. This case highlights the role of imaging in the diagnosis and management of late-presenting CDH. The role of CT imaging as an invaluable tool to further evaluate equivocal radiographic findings in CDH is discussed.