Diabetes-related neuropathic ulcers located at the plantar aspect of the hallux interphalangeal joint are often chronic or recurrent and frequently become complicated by osteomyelitis. Once infected, treatment will typically involve hallux amputation. Although intended as a definitive procedure, amputation of the first toe is not desirable from a cosmetic or functional standpoint and often leads to transfer ulcers at adjacent locations of the foot. Reconstructive wound surgery, combined with limited bone resection, is possible if the infection is caught early before the local tissue and bone have become necrotic. In addition to neuropathy, biomechanical issues, including ankle equinus, hallux limitus, hallux extensus, and hallux valgus, predispose patients with diabetes mellitus to developing plantar hallux ulcers. We commonly employ a proximal based unilobed plantar rotational flap combined with hallux interphalangeal joint arthroplasty as an alternative to hallux amputation. We present a typical case with long-term follow-up to highlight our flap protocol, including patient selection criteria, flap design, surgical technique, bone resection and biopsy pearls, staging timeline, and a typical postoperative course. Periodic follow-up during the next 72 months for unrelated conditions allowed long-term monitoring with no recurrence of osteomyelitis or subsequent amputation. The foot remained ulcer free 6 years later. The benefits of this surgical approach include complete excision of the ulcer, adequate exposure for bone resection, early bone biopsy before the spread of infection or necrosis of local tissue, flap coverage with viable soft tissue, and partial offloading of mechanical pressure at the plantar interphalangeal joint.