Digitally estimating the magnitude of the Plantar Pressures (PP) of the foot is an important aspect in the biomechanical management of diabetic foot and is not yet adopted in our clime and many low income countries mostly due to high cost and complexity of existing designs, as well as poor awareness. This study aimed to produce a cheaper, easier to use and internet of things compliant digital plantar pressure estimating device (DPPE) which should be able to detect, estimate and output in-shoe plantar pressure distribution. 10 Force Sensitive Resistor (FSR) were anatomically spread across an ambipedal insole. ESP8266 board was utilized as the microcontroller. Web applications were designed to ensure a smooth communication between the sensors, the microcontroller, the internet and the display units (Computers and Phones). The device achieved ambipedal fitting, Wi-Fi to internet signal transmissions were successful, and the sensors ability to detect and estimate pressure was achieved. The DPPE as produced in this study can help in achieving digital assessment of the PP estimation and its distribution on the foot for clinical evaluations, hence, it is an important tool in the clinical assessment of the DF managements. Use of WiFi as a mode of data transmission is ideal in a post-COVID world of ours as it supports virtual communication.