Our patient is a healthy, 35–40-year-old male who presented to our clinic in Ventura, California for evaluation of chronic left-sided insertional Achilles pain with no history of trauma. His symptoms began in early adolescence, which limited his participation in competitive sports. He underwent multiple bouts of conservative management, with some periods of respite, but the severity of his pain progressively worsened over time and did not improve with skeletal maturity. On initial presentation to our clinic, he was unable to participate in any form of physical activity and footwear was limited to sandals as any pressure on his posterior heel caused severe pain. Physical examination was notable for a large prominence on the posterior aspect of both heels (A). He experienced exquisite tenderness to palpation of the left posterior prominence. Both feet exhibited full range of motion in dorsiflexion and no weakness in plantar flexion. He had a negative Silfverskiold test. The right sided prominence was asymptomatic. Left ankle weight-bearing radiographs demonstrated a large calcific ossicle within the tendinous insertion of the Achilles onto the calcaneus (A). Interestingly on MRI, the tendon itself exhibited minimal tendinosis with no signs of tendon degeneration. However, there was inflammation at the fibrous site between the ossicle and the calcaneus itself (B and C). Given these findings and the fact that the patient had failed extensive conservative management, surgical intervention in the form of excision of the ossicle itself, debridement, secondary repair of the Achilles tendon, and partial calcanectomy to reshape and contour the bone was planned to provide pain relief, improve function, and allow tendinous healing. The surgical procedure was performed by a foot and ankle fellowship-trained orthopaedic surgeon with assistance from an orthopaedic surgery resident.