Achilles tendinopathy is a common overuse condition that is characterized by degenerative, cumulative tissue microtrauma. It is largely a clinical diagnosis in which the patient typically presents with localized pain that is worse with tendon-loading activities. Imaging modalities may be helpful with the diagnosis of difficult cases or in the planning of interventional procedures. Midportion (noninsertional) and insertional tendinopathy have distinct features and differences for therapeutic paradigms. Overall, Achilles tendinopathy has a good clinical prognosis with most patients improving with activity modification and rehabilitation, with a focus on progressive tendon-loading. Recalcitrant cases may require adjuvant treatment with procedures (e.g., injections, shockwave therapy) and rarely surgical intervention.