The author contends that by reclaiming their own valuable connection to reflective artistic experience and reception, aesthetic theory and art education can contribute to a reconceptualization of autonomy and critique and, perhaps more importantly, to a reorientation of educational practice. Adorno's aesthetics is exceptionally relevant to this aim because his work exemplifies in a unique way the necessary awareness of the antinomic qualities of autonomy and critique, their ineluctable dependence on society and culture, and their secret culpability in domination. The author first examines Adorno's notion of autonomous art and the critical element within it (section 1) and shows how it maps tensions that we encounter in educational discourse as well (section 2). Then (section 3) she moves to the notion of the culture industry and its crucial role for understanding how globalized effects of the systems of money and power regulate and organize free time extra-subjectively, falsely claiming that they thus democratize art. Finally, (section 4) she explains how some contemporary art education renditions play a soporific part instead of awakening the masses from the slumber of passivity and heteronomy. In this vein, injecting Critical Theory aesthetics in the philosophy of education for art proves valuable not only with regard to pupils' relation to art as such but also to the more general educational objective of cultivating reflective and critical subjectivities.