Traditional incision techniques for midfoot amputation might not provide immediate soft tissue coverage of the underlying metatarsal and tarsal bones in the presence of a large plantar soft tissue defect. Patients undergoing transmetatarsal and Lisfranc amputation frequently have compromised plantar tissue in association with neuropathic ulcers, forefoot gangrene, and infection, necessitating wide resection as a part of the amputation procedure. Open amputation will routinely be performed under these circumstances, although secondary healing could be compromised owing to residual bone exposure. Alternatively, the surgeon might elect to perform a more proximal lower extremity amputation, which will allow better soft tissue coverage but compromises function of the lower extremity. A third option for this challenging situation is to modify the plantar flap incision design to incorporate a medial or lateral plantar artery angiosome-based rotational flap, which will provide immediate coverage of the forefoot and midfoot soft tissue defects without excessive shortening of the bone structure. A plantar medial soft tissue defect is treated with the lateral plantar artery angiosome flap, and a plantar lateral defect is treated with the medial plantar artery angiosome flap. Medial and lateral flaps can be combined to cover a central plantar wound defect. Incorporating large rotational flaps requires knowledge of the applicable angiosome anatomy and specific modifications to incision planning and dissection techniques to ensure adequate soft tissue coverage and preservation of the blood supply to the flap. A series of 4 cases with an average follow-up duration of 5.75 years is presented to demonstrate our patient selection criteria, flap design principles, dissection pearls, and surgical staging protocol.