Twenty-two heels in 21 patients treated surgically for a primary diagnosis of insertional Achilles tendinosis were reviewed on the basis of preoperative and postoperative examinations, office records, and a comprehensive questionnaire administered to each subject. Each patient underwent surgical treatment using a midline-posterior skin incision combined with a central tendon splitting approach for debridement, retrocalcaneal bursectomy, and removal of the calcaneal bursal projection as necessary. The findings at surgery revealed involvement of the middle third of the insertion in 21 of 22 cases with only one patient manifesting isolated lateral involvement. Thirteen of 22 had an associated prominent calcaneal bursal projection and four of 22 a superficially inflamed bursa. Three patients required reinsertion of the tendo Achilles via drill holes and one underwent augmentation with a plantaris tendon. Operative findings and complications were reported. Eight male and 13 female patients underwent 22 procedures (one case bilaterally) with an average follow-up of 33 months. Preoperative symptoms include presence of symptoms over a range of three months to two years and pain associated with activities of daily living (17 of 22), limitation of regular activities (six of 22), and pain present at rest in six of 22. Postoperatively, 20 of 22 patients were able to return to work or routine activities by three months; only 13 of 22 were completely pain free. Only 13 of 22 also claimed that they were able to return to unlimited activities. Overall, there was an 82% (18 of 22) satisfaction rate with surgery and 77% (17 of 22) stated they would have the surgery again.