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The care provided for prison leavers with addiction is still very inadequate. In the context of individual empowerment, this article highlights the ambivalences present in the expectations of addiction professionals in terms of motivation and self-reporting, as well as the paradoxical concern with restoring the autonomy of people defined as dependent. It also considers the mechanisms, both internal and external to the institution, that may reduce the residents’ room for maneuver when it comes to the choosing and implementation of projects, despite their being supposedly “individualized.” Finally, it questions the limits of so-called generative policies and the rigidity of care and integration schemes for addicts.