Abstract Heidegger's "Evening Conversation: In a Prisoner of War Camp in Russia, between a Younger and an Older Man" (1945), one of three dialogues composed by Heidegger after the defeat of National Socialist Germany published in Country Path Conversations (Feldweg-Gespräche) explores the being-historical situation and fate of the German people by turning to the early Daoist text of the Zhuangzi. My article traces how Heidegger interprets fundamental concepts from the Zhuangzi, mediated by way of Richard Wilhelm's translation Das wahre Buch vom südlichen Blütenland (1912), such as naturalness, letting/releasement (Gelassenheit/wuwei), the unnecessary (wuyong zhi wei yong) and the useless (wuyong zhi yong) in the context of his hermeneutical and political situation. I consider to what extent this dialogue, along with his other discussions of the Zhuangzi and intensive engagement with the Daodejing from 1943 to 1950, constitute a "Daoist turn" in Heidegger's thinking that helped shape his Postwar thought.