High reoffending rates after release from custody suggest that custodial regimes are not working effectively. An extensive rolling out of rehabilitation programs across the prison estate has not had a great impact on addressing this problem with respect to repeat or habitual offenders. Drawing from script theory, cognitive deficits and offending patterns, I propose that the general thinking style of such offenders is reinforced by the basic arrangement of custodial regimes and, therefore, time being served, unwittingly reinforces the very cognitive processes that lead to an offending cycle. (Published Abstract)