Patients with diabetes and previous history of ulceration occupy the highest category of risk for reulceration and amputation. Annual recurrence rates of diabetic ulcerations have been reported as high as 34%, 61%, and 70% at 1, 3, and 5 years, respectively, with studies reporting 20% to 58% recurrence rate within 1 year. As the ever growing epidemic of diabetes expands globally, this sequelae of diabetic complication will continue to require increasing resources from the healthcare community to effectively manage. Recent data suggest that removal of preventative podiatric care from statewide reimbursement systems lead to significant and sustained increases in hospital admission (37%), charges (38%), length of stay (23%), and severe aggregate outcomes including amputation, sepsis and death (49%). The addition of comorbidities such as peripheral artery disease, poor nutrition, and non-adherence to preventive therapies not only increase a patient's likelihood for ulcer recurrence, but also cost of care and certainty of hospital admission. Currently, numerous efforts, guidelines, and industry generated products exist to prolong remission from ulceration; however, the clinical science for treating this patient population calls for much more effort. Despite this, data continue to suggest to demonstrate that appropriate follow-up care, shoe and insole modification, and patient education play a central role in reducing reulceration and amputation. Novel modalities for offloading and wearable sensor technologies offer the advantage of round-the-clock, patient specific and active response healthcare. These have the potential to detect, or even prevent, many wounds before they begin.