This article demonstrates posterior calcaneal osteophyte excision with Achilles tendon repair in a lightly active male patient in his early 40s, presenting with chronic insertional tendinosis. Following a midline posterior incision, exposure is achieved through a tendon-sparing approach, avoiding cutting or detaching tendon fibers. Complete resection is confirmed via fluoroscopic guidance. The tendon is reattached to the calcaneus using two suture anchors. Preservation of deep tendon attachments, secure fixation, and meticulous wound closure are emphasized, and the patient subsequently experiences an uneventful postoperative recovery. This case highlights key operative steps and decision-making, offering valuable insights for trainees managing similar conditions.