The Smart-Pomodoro system is a wearable study session manager with a visually engaging web application organizer, designed to enhance children’s time management, focus, and commitment to learning. It accomplishes this through the implementation of a user centred interface for caregivers and the incorporation of some gamified features and elements such as progress tracking, a objective-reward system, a point system and a virtual pet that reacts to the child’s work and progress. The study time and the time management aspects are supported by motivational theories, optimized by the implementation of the Pomodoro technique into the child’s work, transforming working into an interactive and pleasurable experience for the child. Additionally, it incorporates a system to increase the caregiver awareness, by analysing the child’s state and the environment context using the smartwatch’s sensors during work. This data can trigger various actions, enabling adaptive responses to different behaviours for a more personalized and effective learning experience, such as positive feedback, session duration changes and personalized questions to boost self-regulation, error correction and time management.