In Japan, civil society uses of online technology have a long history: non-profit computer networks preceded the Internet and webcasting was pioneered by civic groups wanting to overcome rigid broadcasting laws. However, online civil society media face great challenges, with government, market and un-civil society trying to marginalize them against an even more damaging background of general neglect and disregard. The Ministry of Internal Affairs and Communications (MIC) has proposed a new policy framework for the convergence of telecommunication and broadcasting, the basis for a new law planned for 2010. Varying levels of regulation are foreseen for all content. Online variants of mainstream media such as newspapers and television broadcasting will remain largely self-regulated. Civil society media (CSM) remain unrecognized, facing potentially heavy regulation as 'user-generated content'. The authors focus on Japanese online civil society media (online CSM), using case studies to illustrate its successes and challenges in the current environment. In Japan, the Internet is considered the natural domain of business, while civil society, individual, citizens' and personal media, often termed shimin media, are presented as latecomers. The authors will show this to be historically inaccurate and politically dubious. Identifying patterns of enclosure and colonization, the authors argue that despite increases in technological opportunity, the space for civil society media is shrinking, bringing the Japanese media system to a critical juncture. The authors conclude by outlining suggestions for improving the Japanese communication environment to enhance online civil society media.