Chronic disorders of the Achilles tendon are frequently treated by foot and ankle surgeons. A number of surgical techniques have been described for treating chronic degenerative Achilles tendinosis. This is the largest reported series evaluating a method of transferring the flexor hallucis longus (FHL) tendon and securing it with an Arthrex interference screw into the calcaneus. Sixty-two patients with Achilles tendinosis underwent Achilles debridement and transfer of the FHL tendon for chronic conditions when greater than 50% of the tendon was involved. All 62 patients were followed for an average of 26.97 months. A modified American Orthopaedic Foot and Ankle Society score was evaluated both preoperatively and postoperatively and demonstrated significant improvement. Because of the anatomical relationship of the FHL tendon to the Achilles tendon and the fact that both tendons act in the same phase, transfer of this tendon in chronic Achilles tendinosis or rupture is a reasonable option. The described technique is advantageous in that it is simple to perform and is less time-consuming than other reported methods. The authors have had no revisions to date.