We report on the use of free fat grafting as a means of redistributing normal and shear stress after healing of plantar diabetic foot wounds. Although fat augmentation (lipofilling) has been described previously as an approach to supplement defects and prevent atrophy, including use as an adjunct to wound healing and to mitigate pain in the foot, we are unaware of any reports in the medical literature that have described its use in the high-risk diabetic foot in remission. An active 37-year-old man with type 2 diabetes and neuropathy presented with gangrene of his fifth ray, which was amputated. He subsequently developed a chronic styloid process ulceration that progressed despite treatment. We performed a tibialis anterior tendon transfer and total contact casting. He went on to heal but with residual fat pad atrophy and recalcitrant preulcerative lesions. We then used autologous fat grafting for the plantar atrophy. The patient was able to successfully transition to normal shoe gear after 4 weeks with successful engraftment without complication or recurrence of the wound at 6 weeks. This therapy may provide a promising adjunct to increase ulcer-free days to the patient in diabetic foot remission.