OBJECTIVE insertional Achilles tendinopathy is a common condition among athletes and joggers. One fifth of the injuries involves the insertion of the tendon. The etiology is either due to mechanical overuse related to sports activity, or a systemic inflammatory disease. The clinical appearance includes pain and movement restriction. The primary treatment is conservative. The surgery referred to in this study (Calcaneal Osteotomy) is performed by decompression of the posterior margin of the calcaneus. If the tendon is degenerative, debridement is needed. There is controversy on the surgical outcome and the surgical approach. A retrospective analytic observational study. METHODS 20 patients who were diagnosed with IAT (21 feet) and were operated on between the years 2000-2007 by calcaneal osteotomy. METHODS the primary measure of success was diminished pain. It was demonstrated in the AOFAS score and in the VAS scale of pain. RESULTS the average grade in the AOFAS questionnaire improved by 20 points, and the average grading of pain in the VAS scale was decreased by 4.21. The median satisfaction rate was 8, the average was 5.81. 62% of the patients would repeat the surgery/recommend it. We found a significant relationship (p=0.022) between patients who avoided sports activity while suffering from insertional Achilles tendinopathy and the satisfaction rate from the surgery. CONCLUSIONS using the calcaneal osteotomy technique as a surgical treatment for IAT is successful, and improves measures of pain and function. Low compliance with avoiding sports activity while suffering from an IAT might lead to a need for surgery.