With its widespread adoption, the Internet has been looked upon as an agent of change which will shape governance and citizen participation. Mobilization and equalization theories posit that the Internet levels the political playing field by enabling marginalized political groups to overcome barriers such as costs and state control of mass media. This study critically investigates the legitimacy of technologically deterministic claims in a case study analysis of Singapore. In spite of Singapore’s recognized success in harnessing information communication technologies for economic development, the democratizing effects of the Internet have been limited. The method adopted for this paper is two-prong. First, through a case study analysis of the media landscape in Singapore, the paper elucidates on the government’s effective regulation strategy which results in multifarious effects. Second, this paper uses content analysis and structural analysis of party websites to examine how major and minor political parties in Singapore use Internet technology to disseminate their views and engage with citizens.. The findings clearly suggest that the extent to which the Internet can be used as a tool to engender change hinges on not only political culture and the media regulatory landscape, but also on how political parties frame their identities and utilize structural features embedded in Internet technology. In the case of Singapore’s political parties, instead of utilizing Internet technologies to challenge the established status quo, party rhetoric on the World Wide Web engenders a de-equalizing effect that normalizes and stabilizes existing power relations. Politics as usual? Existing studies concerning information communication technologies and political participation have addressed how the technological features of the Internet have enabled different political parties and marginalized groups to further their agendas, mobilize voters and generate political discourse. As the literature review will reveal, a main theme is how the Internet serves as a leveling tool which equalizes power relations among different entities. There appears to be few studies that examine if and how the inherent qualities of party websites may compromise the Internet’s democratizing potential and lead to de-equalizing effects. It is often stated in the literature that websites have the potential to act as mouthpieces and mobilization tools for organizations. Using Singapore as a case study due to its paradoxical state of affairs, this paper examines how different political parties in Singapore use the Internet to communicate to the general public – both in terms of party discourse and structural features. In their study of political websites, Ward, Gibson and Nixon (2003) explain that political websites function as a channel for party administration, campaigning, participation and internal organization, and Resnick (1997) states that websites are often produced with the intention of presenting an