After briefly reviewing the history of penal reform urging an end of barbaric punishment, the author puts flesh on the bones of Foucault’s aesthetic notion of a gentle way of punishment by means of which analogical punishments that fit crimes are invented and applied. Focusing on dehumanizing punishments, generally assaults on dignity and self-worth, the author reveals aspects of gentle tortures experienced by (a) nameless captives in the stone quarries of Syracuse, Sicily during the Peloponnesian War, (b) Vladimir Tchernavin in the infamous Lice Cell in St. Petersburg during Stalin’s purge of scientists, and (c) Gisella Perl who experienced a variety of excremental assaults in Auschwitz and Bergen-Belsen.