We report on a rare case of bilateral ureteral injury in a patient undergoing radical perineal prostatectomy and a unique approach to his treatment. Potential risk factors for such an injury include previous prostatic cryotherapy, transurethral resection, or radiotherapy. Intraoperative recognition of the injury is paramount and may be facilitated by intravenous administration of indigo carmine. While distal ureter ligation, urinary diversion, and delayed ureteroneocystostomy may be regarded as standard management for ureteral injury during radical perineal prostatectomy, this case was treated with a primary bilateral transperineal ureteral reimplantation. Although technically challenging, the described case demonstrates the feasibility and success of such an approach.