Introduction. Delayed healing and recurrence of diabetic foot ulcerations (DFUs) is often related to excessive pressure. Offloading, a mainstay of treatment, can be achieved through a variety of methods. Although pressure mitigation should be continued after wound resolution to prevent recurrence, many offloading modalities are discontinued at that point, with providers instead relying on patient self-directed use of appropriate inserts and shoe gear. Use of a novel offloading modality continued upon wound healing may help break the cycle of recurrent DFUs. Case Report. A patient presented with a 2-year history of recurrent DFU to the right fourth metatarsal head following amputation of the fourth digit. Recurrence continued despite self-reported compliance with therapeutic footwear use. Use of a novel offloading modality that incorporates intermittent pneumatic compression, smart technology for monitoring of patient compliance with use, and the ability to continue therapeutic shoe gear use upon wound resolution was initiated. Wound resolution was achieved, allowing for reconstructive surgery to further mitigate the potential for recurrence. The patient remains free of DFU recurrence for 3 years with continued use of the device’s shoe gear. Conclusions. Implementation of a novel offloading device, which facilitates enhanced perfusion, monitors patient compliance with use, and can be continued upon wound resolution, was able to break the cycle of a recurrent DFU.