Cyber-libertarian discourse has recently made a “come-back” in popular technology and academic discussions about the democratic potential of “Web 2.0.” here, becoming a digital citizen means becoming an autonomous and creative “do-it-yourself citizen-consumer.” This paper identifies some of the limits of this “cyber-libertarian 2.0” discourse. It does so first by drawing upon post-Marxist discourse theory to outline the central elements of the discourse, and second by contrasting the cyber-libertarian understanding of “the situation” with a critical political economy reading that draws upon Debord's theory of “the spectacle.” The comparative analysis is structured by way of the normative categories “liberty,” “equality,” and “the demos,” which both discourses embrace in different ways when speaking of digitally enabled democracy. The critical political economy reading identifies a range of factors limiting the extension of democracy through Web 2.0, factors that are not taken into account by the cyber-libertarian discourse. Identifying such factors provides a starting point for a critical exploration of how democracy can be extended through the Internet. In conclusion, lines for such exploration are suggested, specifically in relation to a radical conception of democracy.