Dreyfus’s work is widely known for its critique of artificial intelligence and still stands as an example of how to do excellent philosophical work that is at the same time relevant to contemporary technological and scientific developments. But for philosophers of technology, especially for those sympathetic to using Heidegger, Merleau-Ponty, and Wittgenstein as sources of inspiration, it has much more to offer. This paper outlines Dreyfus’s account of skillful coping and critically evaluates its potential for thinking about technology. First, it (...) is argued that his account of skillful coping can be developed into a general view about handling technology which gives due attention to know-how/implicit knowledge and embodiment. Then a number of outstanding challenges are identified that are difficult to cope with if one remains entirely within the world of Dreyfus’s writings. They concern questions regarding other conceptualizations of technology and human–technology relations, issues concerning how to conceptualize the social and the relation between skill, meaning, and practices, and the question about the ethical and political implications of his view, including how virtue and skill are related. Acknowledging some known discussions about Dreyfus’s work, but also drawing on other material and on the author’s previous writings, the paper suggests that to address these challenges and develop the account of skillful coping into a wider scoped, Dreyfus-inspired philosophy of technology, it could take more distance from Heidegger’s conceptions of technology and benefit from engagement with work in postphenomenology, pragmatism, the later Wittgenstein, and virtue ethics. (shrink)