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This paper contributes to ongoing debates in the sociology of punishment on how to capture the full complexity of political and policy dynamics that lead to penal outcomes: remaining attuned to broader structural change, while taking seriously the intentions and experiences of penal actors. Theoretically, this paper advocates for a cultural theory approach informed by Mary Douglas’ anthropological work. Drawing in particular on Christopher Hood’s The Art of the State, which applies this approach to organisational studies, I consider how Douglas’ ‘thought style’ categories may help us to make sense of developments in the penal state. Substantively, I draw on work conducted as part of the ‘Rehabilitating Probation’ ESRC-funded project: interviews with national and regional leaders who have overseen a period of dramatic change for probation in England and Wales, which prima facie is an example of ‘Good (but Complicated) Intentions – Disastrous Consequences’ (Cohen, 1985). Probation is considered to be performing very poorly: satisfying neither those who advocate for it to be a desistance-enabling service grounded in its local community, nor those who see it as a risk management body, whose sole focus is public protection. How have we arrived at a situation, after a decade of dramatic reforms, where the organisation is considered by all to be struggling so badly?