Innovation is playing a central role and this is possible due to the remarkable advancements that AI makes it possible. This paper illustrates the development of Artificial Intelligence in educational contexts (AIED) with the use of social robots. There are not many studies in the literature concerning the technology—assessment relationship and about the use of innovative techniques on assessment. Our work tries to propose a contribution by trying to improve school practices focused on assessment, considering pedagogical aspects (HRI—human–robot interaction) by implementing personalized sessions using Pepper as educational technology. An effort will be made to check learners’ progress and to develop innovative formative assessment. This paper introduces a research project which is still in its early stages whose aim is to understand to what extend is Pepper able to provide appropriate situational and emotional feedback to students and foster metacognitive reflections in order to promote mathematics learning.