The ever-increasing use of the internet by terrorist groups as a platform for the dissemination of radical, violent ideologies is well documented. The internet has, in this way, become a breeding ground for potential lone-wolf terrorists; that is, individuals who commit acts of terror inspired by the ideological rhetoric emitted by terrorist organizations. These individuals are characterized by their lack of formal affiliation with terror organizations, making them difficult to intercept with traditional intelligence techniques. The radicalization of individuals on the internet poses a considerable threat to law enforcement and national security officials. This new medium of radicalization, however, also presents new opportunities for the interdiction of lone-wolf terrorism. This dissertation is an account of the development and evaluation of an information technology (IT) framework for detecting potentially radicalized individuals on social media sites and Web fora. Unifying Collective Action Framing Theory (CAFT) and a radicalization model of lone-wolf terrorism, this dissertation analyzes a corpus of propaganda documents produced by several, radically different, terror organizations. This analysis provides the building blocks to define a knowledge model of terrorist ideological framing that is implemented as a Semantic Web Ontology. Using several techniques for ontology guided information extraction, the resultant ontology can be accurately processed from textual data sources. This dissertation subsequently defines several techniques that leverage the populated ontological representation for automatically identifying individuals who are potentially radicalized to one or more terrorist ideologies based on their postings on social media and other Web fora. The dissertation also discusses how the ontology can be queried using intuitive structured query languages to infer triggering events in the news. The prototype system is evaluated in the context of classification and is shown to provide state of the art results. The main outputs of this research are (1) an ontological model of terrorist ideologies (2) an information extraction framework capable of identifying and extracting terrorist ideologies from text, (3) a classification methodology for classifying Web content as resonating the ideology of one or more terrorist groups and (4) a methodology for rapidly identifying news content of relevance to one or more terrorist groups.