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Urethral obstruction is a potentially fatal condition and in cases of recurrent obstruction or an identified cause that is refractory to medical management, a urethrostomy may be performed for definitive treatment. Perineal urethrostomy is the surgical creation of a permanent stoma in the wider pelvic urethra via anastomosis to the perineal skin. Diagnosis of the underlying cause of obstruction, proper perioperative treatment, and an understanding of the anatomy and surgical technique, are imperative to the success of this procedure. This review intends to highlight these aspects, as well as the common complications and expected prognosis to aid decision making in the management of these cases.