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Many transgender men will pursue gender affirmation surgery with metoidioplasty or phalloplasty. This chapter provides an overview of the urethral complications associated with transmasculine genital reconstructive surgery. Reported complications include urethrocutaneous fistulas, persistent vaginal cavities, and urethral strictures. Reconstructive surgery presents a challenge due to decreased blood flow at anastomotic sites and other unique anatomical differences associated with a neophallus. Fortunately, there are several techniques that aid in the management of these complications. However, even after successful reconstruction, urinary incontinence is common. Urologic follow-up is important in managing both expectations and subsequent urologic problems that may require intervention.