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Insertional Achilles tendinosis with Haglund deformity is a common cause of posterior heel pain and the diagnosis can be established by history, physical examination, and imaging. Operative treatment may be required if the conservative treatment has failed. A common surgical procedure usually includes open debridement of Achilles tendon and retrocalcaneal bursa, exostectomy of posterior superior aspect of the calcaneus, and reattachment of the Achilles tendon using a double-row suture anchors. The results of these procedures demonstrated significant improvement of functional outcomes and pain relief with minimal complications.Level of Evidence: Diagnostic Level V. Expert Opinions.