Wounds of the foot challenge reconstructive surgeons to manage multiple factors: sensibility, stability, and durability. In this article, we focus on the insensate foot, which poses challenges to wound prevention with its propensity to develop pressure ulceration. The authors present the innovative use of a pressure-sensing smart insole system (SurroSense Rx, Orpyx Medical Technologies Inc., Calgary, Canada) in the management of the insensate foot in a patient following foot reconstruction. The pressure-sensing smart insole system provided unique feedback to both patient and provider in ways that contributed to the prevention of pressure ulcer recurrence, as well as highlight the importance of prescribed footwear in both the affected and unaffected foot. Wearable real-time monitoring and feedback faces the challenge of patient adherence. Future studies are indicated to examine the specific behaviors that are associated with favorable outcomes and long-term behavior changes.