In the recent study “Ivan Illich Gone Digital: Convivial Information and Communication Technologies for Critical e-Learning” Jandric and Boras (2011) conducted counterfoil research of e-learning technologies. Results of this study strongly indicate that information and communication technologies might possess potentials to develop various radical monopolies, while education might be one of the main vehicles for such developments. Using the aforementioned study as the point of departure, this study confirms that information and communication technologies have the potentials to develop Illich’s radical monopolies and asserts that critical educators have a moral duty to act against such developments. Based on similarity between the position in and against radical monopoly of information and communication technologies and the position in and against the state, it adapts the conclusions developed in 1979 by the London Edinburgh Weekend Return Group to the context of contemporary information and communication technologies. Finally, it identifies oppositional possibilities for critical action against radical monopoly of information and communication technologies in the context of educational praxis.