This study proposes a theorical analysis of the role of self-assessment in the development of the prospective teachers’ reflexive skills and their ability to learn from teaching experience. We identify four conceptions about links between theory and practice in scientific research on teacher education: the reference for self-assessment varies according to the conception one adopts. We then develop a critical analysis of Schön’s and Dewey’s ideas about reflective practice and reflective experience allowing self-regulation of action based on a person’s implication in self-assessment activities. We examine the role of self-assessment as a tool for stimulating reflection about teaching practice. Nevertheless, we warn teacher educators about a pitfall inherent in certification assessment: the paradoxical relationship between learning and getting good grades.