In recent discussions, the role of the Internet in facilitating democratization has been either exaggerated or underestimated. The general consensus seems to be that that the Internet will eventually go the way of other technologies of communication such as the radio and television that failed to live up to their expected role of agents of democratization. Rather than empower marginal groups and constituencies, the Internet could even contribute to more subtle and omnipotent forms of social control through surveillance. This paper examines these positions by focusing on the Singapore case. The possibilities for the expansion of civil society and the emergence of a robust public sphere as a consequence of the wiring up of the country are examined. The key argument of the paper is that although the Internet does indeed contribute to enhanced surveillance capabilities, its potential for circumventing existing forms of regulation and expanding the limited public sphere in Singapore is also very real.