This paper presents "IntuiGeo", a tutoring system for geometry learning in middle-schools on pen-based tablets. The objective is to design an intuitive numerical tool which allows the free drawing of geometric shapes by the simulation of the pen and paper traditional setting. Our approach is based on three main principles. The first one is the online recognition of the user's hand-drawn sketches. The second axis of our approach is the ability of the tutor to supervise the resolution strategy of the pupil in the context of a construction problem resolution. The third principle is the capacity to give real-time visual, corrective and guidance feedback to the pupil to achieve a personalized and autonomous experience. Our system is composed of two main engines. The 2D recognition engine is responsible for the interpretation of the hand-drawn strokes (and has already been validated in [9]). The supervision engine is responsible for the automated generation of a geometry construction problem from a solution example drawn by the teacher, as well as the supervision of the resolution strategies chosen by the pupil. This paper will focus on the concepts associated with the new supervision engine. The first user experiments on the tutor have been conducted in pilot middle-schools in the region of Brittany, France. The analysis of the collected data demonstrates the tutor performance in terms of supervision of the pupils production and its ability to provide pertinent and personalized corrective and guidance feedback.