Abnormal inferior vena cava (IVC) anatomy may present unique challenges for urologists when performing retroperitoneal surgery. Duplication of the IVC is one such anomalous variation and can be found in up to 3% of the population. Misunderstanding of the implications of this aberrant anatomy may lead to intraoperative or postoperative complications. Here, we present two cases of patients undergoing renal surgeries with duplicate IVC. We then review the embryologic origin and anatomic findings in those with abnormal IVC anatomy as well as discuss the surgical implications and considerations for urologists.