It is now widely understood that extremists use the Internet in attempts to accomplish many of their objectives. In this chapter we present a web-crawler called the Terrorism and Extremism Network Extractor (TENE), designed to gather information about extremist activities on the Internet. In particular, this chapter will focus on how TENE may help differentiate terrorist websites from anti-terrorist websites by analyzing the context around the use of predetermined keywords found within the text of the webpage. We illustrate our strategy through a content analysis of four types of web-sites. One is a popular white supremacist website, another is a jihadist website, the third one is a terrorism-related news website, and the last one is an official counterterrorist website. To explore differences between these websites, the presence of, and context around 33 keywords was examined on both websites. It was found that certain words appear more often on one type of website than the other, and this may potentially serve as a good method for differentiating between terrorist websites and ones that simply refer to terrorist activities. For example, words such as “terrorist,” “security,” “mission,” “intelligence,” and “report,” all appeared with much greater frequency on the counterterrorist website than the white supremacist or the jihadist websites. In addition, the white supremacist and the jihadist websites used words such as “destroy,” “kill,” and “attack” in a specific context: not to describe their activities or their members, but to portray themselves as victims. The future developments of TENE are discussed.