Chronic pain in the Achilles tendon is a common problem in both athletes and nonathletes alike. The etiology for the development of Achilles tendinopathy has not been fully elucidated, and there remains multiple theories to explain the pain and dysfunction accompanying this condition. The diagnosis of Achilles tendon problems continues to rely on the clinical history and physical examination. The optimal management of pain, restoration of function, and return-to-sports participation with Achilles tendinopathy are evolving because of the advancement in technologies and research regarding its pathophysiology. This article aims to provide a brief review of the relevant anatomy, differential diagnosis, imaging findings, and an update of the literature on conservative and minimally invasive managements of chronic Achilles tendinopathy.