Because of the importance of technology to the operations of modern terrorist groups, the factors that affect the technological sophistication of extreme organizations are of great interest. In this article, the process through which terrorist groups seek out and deploy new technology is examined by bringing to bear the deep literature that exists on technology adoption by commercial organizations. A framework is described that delineates not only the factors that influence a group’s decisionmaking processes surrounding new technology but also the obstacles that stand in the way of the successful absorption and use of unfamiliar technologies by a terrorist organization. This framework, by taking a holistic view of the entire technology adoption process, sets out a methodology to both more reasonably predict the outcome of a group’s technology-seeking efforts and to speculate about its future innovation efforts. Such a technology focused viewpoint provides a route to more fully inform risk assessment, especially with regard to the low probability-high consequence technologies that have served as the focus of much recent counterterrorist deliberation. The lessons provided by the framework with respect to weapons of mass destruction terrorism and to novel counterterrorist routes are discussed.