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Acquired acro-osteolysis (AOL) is defined as the resorption of bone from the tufts or shafts of the terminal phalanges. Acquired acro-osteolysis can manifest as a primary osteolysis syndrome and also appears in a number of disease states including rheumatologic disorders, neuropathic diseases, the result of prolonged exposure to polyvinyl chloride, and in rare cases, as a response to repeated mechanical stress. In this report, a 46-year-old surfer was evaluated for AOL as a complication of sports-related repetitive trauma to the right second and third toes. Radiography showed the bony tips of his right second and third toes had been eroded away. Acquired acro-osteolysis in the surfer’s toes resulted from increased blood flow initiated to repair microdamage caused by repeated trauma to the distal ends of his second and third right toes due to the habitual dragging of the affected toes across a surfboard. The always initial lytic phase of bone repair was magnified by the increased arterial input to warm the extremities after prolonged exposure to cold. At 6-years’ follow-up, the use of a protective bandage while surfing has permitted full regeneration of the affected toes. (J Am Podiatr Med Assoc 102(2): 165–168, 2012)