Background: Flexor hallucis longus tendon transfer (FHL) with a cortical button tension slide is an innovative addition that has not been measured against traditional methods. Methods: 12 pairs (n=24) of fresh-frozen cadaveric tibia-to-toe samples were used and randomized to receive one of the operative FHL techniques. Specimens underwent bone density analysis. Biomechanical loading was applied between 20 and 60 N at 1 Hz for 100 cycles. Post–cyclic load to failure occurred at 1.25 mm/s. Cyclic displacement, structural stiffness, and ultimate load were derived from load-displacement curves. Student t tests evaluated significant effects between both FHL techniques. Linear regression analysis assessed interactions between bone density and strength of FHL technique. Results: Average tendon diameter was 5.44±0.46 mm. Average bone density was 1.06±0.08 g/cm2. Addition of a cortical button to FHL transfer did not significantly affect cyclic displacement (0.78±0.52 mm vs 0.87±0.80 mm) or structural stiffness (162.11±43.34 N/mm vs 167.57±49.19 N/mm). Cortical button addition to FHL transfer resulted in significantly increased ultimate load (343.72±68.93 N) compared with interference screw alone (255.62±77.17 N) ( P = .0002). Linear regression analyses did not reveal any significant interactions between bone density and FHL tendon transfer technique. Conclusion: Enhanced strength can be achieved with FHL tendon transfer to calcaneus using an interference screw and cortical button tension slide technique as compared to an interference screw alone. Cortical buttons in the setting of FHL tendon transfer to the calcaneus offers an additional level of support. Clinical Relevance: Operative cases presenting with poor bone quality due to osteoporosis or osteopenia could benefit from cortical button fixation during FHL transfer. Clinical studies are needed to determine if the increased construct stability conferred from the additional use of a flip button results in fewer FHL transfer failures or better clinical outcomes. Level of Evidence: Level V, Controlled Laboratory Study.