The painful ankle arthrodesis is an unsolved clinical problem. In many cases, transtibial amputation may be the best option for functional recovery. Recent reports of early success with second generation ankle implants show takedown of the problematic ankle fusion and conversion to total ankle arthroplasty may be an alternative to amputation. This study is a retrospective review of 23 ankles in 22 patients scheduled to have this procedure. Four patients were lost to followup, leaving 19 ankles in 18 patients at an average followup of 39 months. Three patients chose to have an amputation because of continued pain. In the remaining 16 ankles, the mean AOFAS ankle-hind foot outcome score improved from 42-68. Patients who had a clear source of pain with the ankle arthrodesis (such as subtalar arthrosis) had a better result than patients without a clear source of pain. All the patients who had the lateral malleolus resected during previous arthrodesis had complicated courses after arthroplasty. For patients with a definable source of pain and who have not had previous malleolar resection, conversion of a failed ankle arthrodesis to total ankle arthroplasty may be a viable alternative to amputation.