The main objective of this work is to develop a technological solution to support active aging of frail older individuals. In this perspective, we designed a connected insole in order to encourage frail elderly persons to become more active in their daily life. The project presented in this paper, funded by the French National Research Agency, aims to design and evaluate an original solution to follow and encourage walking activity. The evaluation is performed in two stages: adjusting tests in a living-lab with nine healthy elderly, then clinical evaluation of three frail patients followed over one month. We designed a noninvasive wireless insole, which automatically measures gait parameters and transmits information to a remote terminal via a secure Internet connection. The first laboratory tests of this technological solution showed good reliability measurements as well as good user acceptability. The average distance error obtained on volunteers is 3.2% and the accuracy of the average walking speed is 96.8% thanks to design of a calibration system based on a personalized stride length measurement. Finally, the introduction of an induction charging instead of a button cell makes the system perfectly autonomous. In this paper, we present the specifications of the solution, the design of the connected insole, the methods used to measure desired parameters, the results of the living-lab tests, and the work in progress.