We report the case of a female with recurrent venous thromboembolisms (VTEs) despite being appropriately anticoagulated. Different anticoagulants were trialed and all led to treatment failure. As a result, the patient was started on dual anticoagulation with warfarin and apixaban. There were no recurrences of clots while the patient was adherent to dual anticoagulation. This case report adds to current literature demonstrating the efficacy of dual anticoagulation in patients with recurrent VTE who fail single-agent therapy. It also demonstrates the need for additional studies that evaluate the utility of dual anticoagulants as a treatment modality for patients failing monotherapy.