The question of the contemporary relevance of Heidegger's reflections on technology to today's advanced technology is here explored with reference to the notion of ''entanglement'' towards a review of Heidegger's understanding of technology and media, including the entertainment industry and modern digital life. Heidegger's reflections on Gelassenheit have been connected with the aesthetics of the tea ceremony, disputing the material aesthetics of porcelain versus plastic. Here by approaching the art of wabi-sabi as the art of Verfallenheit, I argue that Gelassenheit may be understood in these terms.