Heel raise is widely prescribed to patients with chronic ankle instability in order to strengthen the Peroneus Longus muscle (PL) which supports the weakened lateral collateral ligaments. While the exercise itself is intuitive, ankle orientation is of particular importance because heel raises performed with inversion do not well recruit the PL. This implies that proper execution is imperative and a means to assess heel raise training sessions is needed. In this study we present a smart insole system is capable of identifying heel raise events and its corresponding rise, hold and drop phases, which allows for a more descriptive analysis. The results from our heel raise sessions, which consist of four different variants performed by five healthy subjects, suggest that medial-lateral foot pressure distribution and foot orientation are needed to differentiate heel raises performed with ankle eversion and inversion. We go further and substantiate that proper execution, detected by our system, indeed leads to increased PL activation by analyzing the electromyography signals. We believe that the proposed system may provide clinicians with invaluable information regarding onsite as well as at-home training and possibly with biofeedback serve as foundation for software as a medical device.