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In this article, we will seek to examine the question of the meaning of punishment in relation to crime and incarceration. From the punishment of deprivation of liberty to social reintegration, the sentence appears to have “repressed” its second objective, namely the amendment of the offender, or even moral regeneration. Moreover, in the judicial field, the introduction of the individualization of sentences seems to have completely obscured the question of the singularity of sentences. Thus, following a brief historical review, we indicate the extent to which clinical practice in prison demonstrates this failure: the loss of detainees, with regard to the meaning given to their conviction –if they have been convicted–, to their incarceration, and especially to their sentence, is obvious. Between the nonsense, the enigma, and the impossible, two major questions form the basis of our work: What is a crime and what is a punishment? And what does clinical practice in prison teach us about crime and punishment, situated as it is in the gap between the two?