This chapter examines the writing produced by various Islamic State affiliates in English so as to disentangle the relationship between the writing and radicalization. Radicalization of individuals to violent action or the support of violent action presents an almost impossibly complex problem for study. The conventional wisdom put forward by Ingram that propaganda contributes to radicalization is pervasive throughout the literature on atrocities. The internet has changed the image, means and reach of jihad. Jihad is no longer confined to radio and newspaper calls. The online presence of fighters and sympathizers has inevitably promoted the spread of Islamist principles and its political and religious doctrine in support of militant jihadism. The information–motivation–behavioral skills framework has received extensive empirical support across a wide range of behavior-change intervention applications and contexts. Blending a quantitative approach that extracts, classifies, and quantifies linguistic metaphors with a qualitative analytic approach allows to better understand how different motivational strategies might be enacted in propaganda.