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Ankle sprains are a common injury among physically active populations and occur with an incidence of around 2.15 per 1000 person-years. This article discusses various surgical procedures used to treat chronic lateral ankle instability, including direct ligament repair, anatomic reconstruction, and nonanatomic reconstruction. We focus our discussion on the most common and challenging complications of ankle stabilization, both in our experience and as supported by the existing literature, including recurrent instability, superficial peroneal nerve injury, and unaddressed pathology that continues to cause symptoms and limit function. We offer possible methods to manage these conditions as well as available outcome data.