Scholars depict punishment as a moral dialogue between the community and the offender, which addresses both the offender’s crime and character. However, how the penal message evolves vis a vis that crime and character as it passes through the different stages of the criminal process has remained under-theorized. This article, building on communicative theory, explores the interrelation between crime and character along the penal process, from sentencing, through prison, to parole release. We argue that in the penal dialogue the relationship between crime and character evolves in a dynamic way through three phases: separateness (sentencing), fusion (prison), and re-distinction (parole) of crime and character. The proposed analysis develops the communicative meaning of the penal process, provides a normative account of the work of punishment administration authorities, and explores applications of our proposed normative analysis for the administration of the punishment.