Terrorists and extremists are increasingly utilizing Internet technology to enhance their ability to influence the outside world. Due to the lack of multi-lingual and multimedia terrorist/extremist collections and advanced analytical methodologies, our empirical understanding of their Internet usage is still very limited. To address this research gap, we explore an integrated approach for identifying and collecting terrorist/extremist Web contents. We also propose a Dark Web Attribute System (DWAS) to enable quantitative Dark Web content analysis from three perspectives: technical sophistication, content richness, and Web interactivity. Using the proposed methodology, we identified and examined the Internet usage of major Middle Eastern terrorist/extremist groups. More than 200,000 multimedia Web documents were collected from 86 Middle Eastern multi-lingual terrorist/extremist Web sites. In our comparison of terrorist/extremist Web sites to US government Web sites, we found that terrorists/extremist groups exhibited similar levels of Web knowledge as US government agencies. Moreover, terrorists/extremists had a strong emphasis on multimedia usage and their Web sites employed significantly more sophisticated multimedia technologies than government Web sites. We also found that the terrorists/extremist groups are as effective as the US government agencies in terms of supporting communications and interaction using Web technologies. Advanced Internet-based communication tools such as online forums and chat rooms are used much more frequently in terrorist/extremist Web sites than government Web sites. Based on our case study results, we believe that the DWAS is an effective tool to analyse the technical sophistication of terrorist/extremist groups’ Internet usage and could contribute to an evidence-based understanding of the applications of Web technologies in the global terrorism phenomena.