The chapter explores what is meant by the ‘supervision of sentences’ and the relationship between the European Convention on Human Rights and the execution of prison sentences that have been lawfully imposed by national courts and the acceptability of whole life sentences and the legality of the deprivation of liberty under both Articles 3 and 5 ECHR. This chapter stresses that, while the ECtHR has rendered tough judgments in some cases, it has also attempted to soften and mitigate those judgments by delivering opposite judgments and allowing member states a significant margin of appreciation and residual competence. In this respect, we reflect on the contradictions these judgments give rise and the oscillations between risk management and punitiveness. We also show that the reliance on varied risk management techniques has reactivated the old surveillance rationality through the traditional panopticon conceptualised by Foucault. Rather, we assume that risk management is diverse and oscillates between an actuarial risk based-approach and an assessment of dangerousness. Against the inverted panopticon and whereas certain national administrations are scrutinised by the ECtHR and the Committee of Ministers concerning their potential breaches of the right to liberty and the right to dignity, certain prisoners are subjected to regular surveillance of their profiles and deeds through risk management techniques and their data management.