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In the theoretical desistance literature strong claims are made that prisoners expectations are an important factor for the desistance process. Empirical evidence of that claim is, however, scarce. The aim of this paper is to examine prisoners’ expectations regarding future criminal behavior before they are released, and whether or not these expectations come true after their release from prison. The expectations examined are on chances of reoffending, re-arrest and re-incarceration for a variety of different types of crime. Individual factors mediating and moderating the relationship between inmates’ expectations and their future criminal activities will also be examined. The data analyzed come from the Prison Project, a nationwide panel study of Dutch prisoners (N=1,904). The data include detailed information on prisoners expectations as well as on registered and self-reported recidivism patterns over a two-year post-release period. The findings indicate a clear association between prisoners expectations and their future behavior. The paper concludes with an discussion of the implications for sentencing and detention policies.