Critical reflexivity has been acknowledged as fundamental in higher education. For facing complex situations in turbulent environments, students nowadays need not only to be taught technical knowledge, but also to be helped develop "relevant" learning for their future professional practice. In recent years, scholars have concentrated on what makes the internship experience a successful opportunity for the parties involved, and have also discussed the crucial role of a mentor/tutor in sustaining relevant and effective learning. However, the specific conditions that make tutorship successful in promoting critical reflexivity in such a boundary crossing experience need to be further explored. Aim of this paper is therefore to analyze what tutorship conditions sustain the development of critical reflexivity in internship. For this purpose, we will present the case study of an internship program run by one of the largest universities in northern Italy.