Prisons can play a critical role in both triggering and reinforcing the radicalization process. The prison’s isolated environment, ability to create a ―captive audience‖ atmosphere, its absence of day-to-day distractions, and its large population of disaffected young men, makes it an excellent breeding ground for radicalization. The goal of this presentation is to describe the internal radicalization process among prison inmates and understand the numerous challenges posed by radicalization behind bars. In the first part of the presentation, we will analyze those challenges and portray the current situation in European and American jails. We will then, explore a few case studies, including ―the Shoe Bomber‖ case involving Richard Reid, the ―Jose Padilla‖ case and the less familiar cases of Jose Emilio Suarez Trashorras and Safe Bourada and others. To conclude the presentation, we will suggest prospective policy options and recommendations to overcome this growing phenomenon.