Transfer ulcers beneath the second metatarsal head are common after diabetes-related partial first ray amputation. Subsequent osteomyelitis of the second ray can further complicate this difficult situation. We present 2 cases depicting our plantar rotational flap technique for revision surgery involving conversion to either panmetatarsal head resection or transmetatarsal amputation (TMA). These cases are presented to demonstrate our indications, procedure selection criteria, flap technique, operative pearls, and staging protocol. The goals of this surgical approach are to excise and close the plantar ulcer beneath the second metatarsal head, remove any infected bone, allow staged surgery if needed, remove all remaining metatarsal heads to decrease the likelihood of repeat transfer ulcers, preserve the toes when practical, avoid excessive shortening of the foot, avoid multiple longitudinal dorsal incisions, and create a functional and cosmetically appealing foot. The flap is equally suited for either panmetatarsal head resection or TMA. The decision to pursue panmetatarsal head resection versus TMA largely depends on the condition of the remaining toes. Involvement of osteomyelitis in the base of the second proximal phalanx, the soft tissue viability of the remaining toes, the presence of a preoperative digital deformity, and the likelihood that saving the lesser toes will be beneficial from a cosmetic or footwear standpoint are factors we consider when deciding between panmetatarsal head resection and TMA. Retrospective chart review identified prompt healing of the flap in both patients. Neither patient experienced recurrent ulcers or required subsequent surgery within the first 12 months postoperatively