Perineal urethrostomy is considered to be the last option to restore voiding in complex/recurrent urethral stricture disease. It is also a necessary procedure after penectomy or urethrectomy. Stenosis of the perineal urethrostomy has been reported in up to 30% of cases. There is no consensus on how to treat a stenotic perineal urethrostomy, but, in general, a form of urinary diversion is offered to the patient. We present the case of a young male who underwent perineal urethrostomy after urethrectomy for urethral cancer. The postoperative period was complicated by wound dehiscence with subsequent complete obliteration of the perineal urethrostomy. Revision surgery was performed with reopening of the obliterated urethral stump and coverage of the skin defect between the urethra and the perineal/scrotal skin with a meshed split-thickness skin graft. To date, this patient is voiding well and satisfied with the offered solution.