Tarsal tunnel syndrome results from posterior tibial nerve entrapment beneath the flexor retinaculum and the deep fascia. The syndrome consists of pain, paresthesias, and vasomotor changes. Surgical correction via release of the flexor retinaculum is the treatment of choice. There is however, a 10% to 20% failure rate, with little in the literature addressing treatment options in this subset of individuals. Two patients with recurrent tarsal tunnel syndrome were treated with re-release of the retinaculum, followed by nerve coverage with a radial forearm free flap. At 15 and 27 months, both patients were pain-free, ambulatory, and able to return to work.