<p>This article revisits John Haugeland’s early work on natural language understanding to address contemporary debates about large language models and their capacity for genuine understanding. Through a reinterpretation of Haugeland’s essay “Understanding Natural Language” via key notions in the thought of Martin Heidegger, the article argues that world-disclosing care and the capacity for taking responsibility—what Haugeland calls “giving a damn”—are the conditions of possibility for understanding. By contrasting additive and transformative approaches to understanding, the paper highlights the ontological stakes underpinning contemporary debates about understanding in AI. It concludes by situating the framework Haugeland calls “existential holism” as an overall critique of additive theories.</p>