Diabetic foot manifests as one of the major complications of diabetes. It is notably characterized by abnormally elevated local plantar pressure in its early stages. Since its early symptoms are hard to notice, many patients delay treatment until the state of symptom becomes severe, when it may be too late to prevent amputation. This paper aims to resolve this clinical dilemma by developing early warning mechanisms for plantar pressure alterations in diabetic foot patients, with particular emphasis on the transitional dynamics and early-warning threshold values between normal and pathological foot pressure. The paper collected plantar pressure data from both control and diabetic foot groups, which enabled not only the evidence-based early-warning thresholds but also the development of a remote monitoring system incorporating an iterative warning algorithm. Bench testing and clinical trials verified the system’s robust performance and demonstrated high accuracy of its warning algorithm.