This paper inquires into a practical logic of what can be called socially just education in late modern societies, based on a reexamination of critical pedagogy, and clarifies the boundary-crossing nature of this education and the dilemmas that it inevitably entails. The discussion first addresses and reexamines certain oppositional arguments made by the most influential authorities of critical pedagogy, Michael Apple and Henry Giroux, to discern the directionality for a practical logic of socially just education. Second, to underpin the theoretical considerations, the paper refers to Nancy Fraser's concepts of social justice--the politics of recognition, redistribution, and representation--and, by reinterpreting the politics of redistribution based on the theory of cultural capital of Pierre Bourdieu, seeks to construct the vital part of a practical logic of socially just education in late modernity. To complement this model, the paper invokes Gert Biesta's discussion of how schools should teach democracy. Last is an overview of the dilemmas that must be faced when attempting to put socially just education into practice in the late modern era, along with proposed guidelines for tackling these dilemmas.