As an antithesis of “authoritarian enclave” which has been well-established in the comparative politics literature, “democratic enclave” points to the institution of a state or the unambiguous regulatory space in society “where the authoritarian regime’s writ is substantively limited and is replaced by an adherence to recognizably democratic norms and procedures” (Gilley 2010). In this sense, the Internet space, embodied by information and communication technologies, has great potential to play such a role, since its “inherited” properties of decentralization and anonymity would inevitably breach the authoritarian rules. However, a closer look at three Southeast Asian states, Malaysia, Singapore and the “New Order” Indonesia whose regimes were characterized by authoritarianism when Internet was initially developed, reveals different trajectories. In the “New Order” Indonesia and Malaysia, the governments consciously left the Internet space uncontrolled; the online media developed independently, vibrantly, and professionally, especially in the Malaysian case; and there were strong connections between online and offline contentious politics. These elements made the Internet space in Indonesia and Malaysia a successful case of democratic enclave. Based on these criteria, however, the Internet space in Singapore has not achieved similar status. This paper analyses the different outcomes of enclave creation on the cyberspace among these countries. It argues that elite conflict and the strength of civil society are the two major factors that shape the differences. In this sense, the political contexts are of great importance for the understanding of Internet’s political impacts.