Artificial intelligence is profoundly transforming the world in various spheres and already finding its way into educational institutions. This essay aims to examine whether the Deweyan ideal of education can be achieved through such digital means. By analyzing how both the aims and means of education, as defined by Dewey, can be understood in the context of learning with artificial intelligence, the inherent differences of both educational approaches are brought out. It becomes apparent that important concepts that characterize successful education for Dewey, such as intrinsic inquiry, experience-based schooling, and thinking as the method for learning, do not go hand in hand with intelligent teaching systems.