Work on preventing radicalization and violent extremism (PRVE) is beset with dilemmas, difficult considerations and pitfalls. Based on a synthesis of previous research and original data, this article conceptualizes and discusses three key dilemmas present in PRVE practice and policy: that of civil liberties versus security, that of too soft versus too hard measures, and that of intention versus outcome. The article illustrates how these dilemmas play out and are deliberated upon by PRVE practitioners and policymakers in Nordic countries. The exploration of these dilemmas and the different action pathways they involve can function as “sensitizing tools” to encourage reflexivity around the complexity and unintended consequences of PRVE. The dilemmas also reflect broader issues of societal and scholarly importance, as they make evident several critical ramifications of PRVE.