Recurrent male anterior urethral stricture disease is a complex surgical challenge that should be managed by reconstructive urologists with experience in stricture management. Diagnosis of recurrence requires both anatomic narrowing and patient symptoms identified on validated questionnaires, with limited role for intervention in asymptomatic treatment "failures". Endoscopic management has a very specific role in recurrence, and the choice of technique for urethroplasty depends on pre-operative urethrography and cystoscopy. Surgical success depends on addressing patient concerns, complete stricture excision, tissue quality optimization, and the use of multi-stage repair when indicated. Augmentation with genital skin flaps and/or grafts is often required, with buccal mucosa as the ideal graft source if local tissue is compromised. Salvage options including urinary diversion and perineal urethrostomy must also be considered in debilitated patients with severe disease or repeated treatment failures. Unique patient populations including patients with hypospadias and lichen sclerosis are among the highest risk for repeated recurrence and require special care in surgical technique, graft selection, and post-operative management.