Despite advancements in the treatment of diabetic patients with “at-risk” limbs, minor and major amputations remain commonplace. The diabetic population is especially prone to surgical complications from lower extremity amputation because of comorbidities such as renal disease, hypertension, hyperlipidemia, microvascular and macrovascular disease, and peripheral neuropathy. Complication occurrence may result in increases in hospital stay duration, unplanned readmission rate, mortality rate, number of operations, and incidence of infection. Skin flap necrosis and wound healing delay secondary to inadequate perfusion of soft tissues continues to result in significant morbidity, mortality, and cost to individuals and the health-care system. Intraoperative indocyanine green fluorescent angiography for the assessment of tissue perfusion may be used to assess tissue perfusion in this patient population to minimize complications associated with amputations. This technology provides real-time functional assessment of the macrovascular and microvascular systems in addition to arterial and venous flow to and from the flap soft tissues. This case study explores the use of indocyanine green fluorescent angiography for the treatment of a diabetic patient with a large dorsal and plantar soft-tissue deficit and need for transmetatarsal amputation with nontraditional rotational flap coverage. The authors theorize that the use of indocyanine green may decrease postoperative complications and cost to the health-care system through fewer readmissions and fewer procedures.