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Achilles tendon pathology is common and affects athletes and nonathletes alike. The cause is multifactorial and controversial, involving biological, anatomical, and mechanical factors. A variety of conditions characterized by Achilles tendon inflammation and/or degeneration can be clinically and histologically differentiated. These include insertional Achilles tendinopathy, retrocalcaneal bursitis, Achilles paratenonitis, Achilles tendinosis, and Achilles paratenonitis with tendinosis. The mainstay of treatment for all of these diagnoses is nonoperative. There is a large body of evidence addressing treatment of acute and chronic Achilles tendon ruptures; however, controversy remains.