Physical rehabilitation therapies for children present a challenge, and its success—the improvement of the patient’s condition—depends on many factors, such as the patient’s attitude and motivation, the correct execution of the exercises prescribed by the specialist or his progressive recovery during the therapy. With the aim to increase the benefits of these therapies, social humanoid robots with a friendly aspect represent a promising tool not only to boost the interaction with the pediatric patient, but also to assist physicians in their work. To achieve both goals, it is essential to monitor in detail the patient’s condition, trying to generate user profile models which enhance the feedback with both the system and the specialist. This paper describes how the project NAOTherapist—a robotic architecture for rehabilitation with social robots—has been upgraded in order to include a monitoring system able to generate user profile models through the interaction with the patient, performing user-adapted therapies. Furthermore, the system has been improved by integrating a machine learning algorithm which recognizes the pose adopted by the patient and by adding a clinical reports generation system based on the QUEST metric.