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Policy-makers who are confronted with the potential spread of violent extremist ideologies among prison inmates are challenged to design sustainable prison regimes which are suitable to counter prison radicalisation whilst rehabilitating and reintegrating inmates into society. This article outlines a theoretical framework that explains how uncertainty and pressure in the policy-making context heightens the need for structure that induces a shift towards intolerance and stereotypic black-and-white thinking, which leads to the introduction of unbalanced, one-sided prison regimes. We argue that in the long run, these prison regimes are likely to be self-undermining and unsustainable because they undermine long-term security objectives and cause undesired side effects. These propositions are illustrated by an in-depth case study of the Dutch terrorist detention policy