The article claims that Arendt’s engagement with judgment has a double origin: She approaches judging first of all as an ethical problem posed by the massive breakdown of personal judgment – the capacity to distinguish right from wrong – in the Third Reich. On the other hand, she addresses judgment as an ‘epistemological’ challenge: as the question of how one is to judge this massive breakdown in the capacity for judgment during the Third Reich itself; and, how one is to judge that which is historically ‘novel’ in totalitarianism: morally, juridically, philosophically, politically, historically. The article argues that, from The Origins of Totalitarianism onward, Arendt dedicated her thought and writing to answering this double challenge of judgment (through the rupture in civilization in the extermination of the Jews on the one hand, and through the rupture in tradition of Modernity on the other). This also means: She dedicated her thought and writing to the attempt to prove her own judgment in practice, to put it to the test in her own modes of writing.