Ankle sprain is probably the most commonly encountered injury in athletes. High ankle sprain, however, is much less common and its clinical presentation can be subtle in the absence of periarticular fracture. A clear understanding of anatomy and biomechanics and a high index of suspicion are important in the timely recognition of this injury. Delays in diagnosis and treatment often lead to a protracted course of recovery and long-term disability for the athletes. A lot of progress has been made in the diagnosis and treatment of high ankle sprain since Dr. Amendola's article on "Controversies in Diagnosis and Management of Syndesmosis Injuries of the Ankle" in Foot and Ankle in 1992. Criteria for the diagnosis of high ankle sprain have become much better defined. There are more specific recommendations on treatment guidelines regarding transsyndesmotic stabilization. However, issues that remain controversial include clinical and radiographic assessment and documentation of syndesmosis instability, types of transsyndesmotic fixation materials, the role of arthroscopic surgery in the management of acute and chronic syndesmotic injuries, treatment for chronic or recurrent diastasis, alternatives for syndesmotic and tibiotalar arthrosis, and therapeutic protocol for competitive high performance athletes. As the understanding on this subject grows, much more basic science and clinical research are needed to study the distal tibiofibular joint, which indeed is a complex articulation with poorly understood biomechanics.