Throughout this working paper, under the scope of Prison Reform and Proposals of Prison Reform in Belgium and in Portuguese Prison System, between the periods of 2004 up to 2006, one is driven by the inseparability of Rehabilitative philosophy with Harm Reduction strategies.Whether Belgium, whether Portugal strongly tend to believe that the rehabilitative rationale is a must once speaking of a custodial sentence. Alike, in both countries, it is up to the State to ensure Rehabilitation as an inexorable part of execution of sentences. Overall, both States dismiss of a paternalist approach towards the inmates, namely through the Individual Detention Plan. Nevertheless, in Belgium, Rehabilitation within doors of the offender seems to go hand in hand with the need of doing Reparation towards the victim. Albeit the different political organization as far as execution of sentences is concerned, both Prison System of Belgium and Portugal seems to be constrained with similar defaults such as the lack of proper methodologies and of "follow up " measures. Yet, the recent developments in both countries do not seem to give concrete added value towards those points. Furthermore, the author of this working paper tries to answer to some of the following questions: Rehabilitation - Is it or is it not a consensual concept? Which other concepts may be intrinsically related to rehabilitative intervention when one is speaking about rehabilitation within prison environment? Which factors may play a role, as likely to facilitate or hamper rehabilitative languages, within the prison context? Beyond that, some possible missing items of the reforming documents are also appointed.