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Although straightforward male urethral stricture disease is commonly encountered in the scope of general urologic practice, complex urethral strictures are less common and require a more systematic approach. Complex urethral stricture surgery for long and panurethral strictures, after failed hypospadias repair, and for recurrent posterior urethral distraction defects requires a dynamic treatment paradigm. A multistaged urethral reconstruction is often necessary owing to hostile urethral tissue, especially after multiple previous procedures. A perineal urethrostomy sometimes offers improved quality of life for patients with complex urethral stricture disease, particularly if they have undergone previous failed repairs. Recurrent posterior urethral distraction defects are best treated with excision of the scarred urethral segment and re-anastomosis. Urethral stricture disease after treatment for prostate cancer requires multiple treatment approaches given the often poor tissue quality and likelihood of stricture recurrence.