In this paper, we present the design and development of a smart insole that may be used to assess long term chronic conditions that affect the elderly population such as Stroke, Dementia, Parkinson;s disease, Cancer, Cardiac Disease and Diabetes. This smart insole offers the potential for evidence base rehabilitation. The ICT solution detect the plantar foot pressure in a free living context through the integration of piezo sensors, microcontroller and Bluetooth technology to empirically measure the pressure at important pressure points. The insole consists of 32 piezo sensors, 01 tri-axial accelerometers, temperature sensor and force sensor to automatically switch ON/OFF the insole. The accelerometers provide context for orientation. The design comprises two flexible PCBs encased in a padded layer, in order to protect the sensors and provide comfort to wearer.