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Caudal duplication syndrome is an exceedingly rare condition that manifests as duplicative anomalies of the gastrointestinal and genitourinary systems. We present a case of an adult patient born with multiple congenital anomalies including duplicated reproductive and urinary systems. She presented to our center for initial evaluation 11 years ago largely experiencing right-sided pelvic organ prolapse and bilateral urinary tract voiding dysfunction. She underwent successful surgical management and presented several years later for recurrent symptoms. We describe her presentation and our surgical experience, including complications and outcomes, for this case. We also review caudal duplication syndrome—its etiology, clinical presentation, diagnostic workup, surgical intervention (if any), and recommendations.