Despite shared history and a common ambition to comply with European standards, post‐Soviet countries differ in the way in which they reform prisons. By investigating two most‐similar cases of policy transfer from Norway – the establishment of the Olaine Drug Centre in Latvia and the Pravieniškės Drug Unit in Lithuania – this article explains why outcomes diverge and how Western‐European carceral individualism clashes with path‐dependent carceral collectivism. Where leadership is unstable, with limited powers, the informal legacies are strong, and policy‐transfer strategy is fragmented, as in Lithuania, the outcome is likely to be non‐transformative. Where, on the contrary, leadership is stable, enjoying larger discretionary powers and the intervention strategy is holistic, as in Latvia, the import of foreign institutional models is likely to be successful.