Urethral prolapse is a rare and benign condition where the inner urethral lining protrudes through the external urethral opening. This condition is mostly seen in prepubertal and postmenopausal women. Risk factors include obesity, multiparity, and the onset of menopause. It has a low occurrence, resulting in frequent underdiagnosis. This is compounded by its typical delayed diagnosis. We present a case of a 71-year-old postmenopausal woman who presented with persistent urinary symptoms. After multiple failed conservative treatments, she underwent a successful urethral prolapse excision. Our case highlights the importance of considering urethral prolapse as a differential diagnosis in a postmenopausal woman with continual urinary symptoms.