Critical reflection in teachers' professional development has received much attention in the scholarly literature, and there is an overwhelming consensus about its great significance to the quality of teachers' work. Nevertheless, despite the well-established role of reflection, a large gap between the professed goals and the actual reflective practice of teachers remains. The article starts with a short overview of the different definitions of critical reflection in the context of teachers' professional development and then underlines some empirical research findings on the problems that teachers and teacher educators face when putting reflective practice into practice, especially at the deeper and more complex levels of reflection. It continues with a consideration of teachers' qualifications for in-depth reflection as well as the obstacles and challenges facing teachers and teacher educators. The obstacles occur at the level of individual teachers' personal traits and at the level of the context in which reflection is done. Employing an analysis of the obstacles, the authors develop some guidelines on how to support teachers in their attempts at making critical reflection part of their teaching practice. It is crucial for this encouragement not to overlook the principal purpose of teachers' critical reflection; to contribute to new insights, knowledge reframing, and the introduction of such changes in teaching that will support students' learning and the development of the community for the better learning, work, and life of all its individuals.