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As part of the NSF-funded Dark Web research project, this paper presents an exploratory study of cyber extremism on the Web 2.0 media: blogs, YouTube, and Second Life. We examine international Jihadist extremist groups that use each of these media. We observe that these new, interactive, multimedia-rich forms of communication provide effective means for extremists to promote their ideas, share resources, and communicate among each other. The development of automated collection and analysis tools for Web 2.0 can help policy makers, intelligence analysts, and researchers to better understand extremistspsila ideas and communication patterns, which may lead to strategies that can counter the threats posed by extremists in the second-generation Web.