This text discusses today's digital transformation through the lens of Horkheimer and Adornos’ study of the enlightenment. Policy and public discourse around digitalisation embrace and adhere to the narrow tenets enlightenment thinking; the idea that rationality, individual freedom, and a society free from superstition are necessary and attainable goals. The costs of what has come to be called ‘Modernity’ are many. Through the application of rationality to all spheres of life, married with disruptive technological advancement, humanity has diminished its’ imagination – its ability to seek new directions. To paraphrase Horkheimer and Adorno, Modernism fights against nature, of which we are a part, and thus, paradoxically, sets us in a fight against ourselves. Environmental degradation, the price of progress, being just one example of this – deadening work, consumerism and severed social connections being amongst others. In this framing, digitalisation itself comes to be understood itself as akin to a force of nature – one that we can do little about, other than adjust and adapt or be swept away. But this by no means a foregone conclusion, there is light at the end of the optical fibre. Albeit that recent technical developments around artificial intelligence appears to be pushing policy makers into hasty decisions, the pace of the technical development is not as fast as we believe, and in comparison with the Reformation – we have time. If we can restrain ourselves from the resist, adapt or die responses promoted in popular discourse in face of the shock of large language models and rising threat of automation, then we create room to consider economic, social, and ecological alignment and accord, in the decision making and design of future interactive artefacts and digital services. The article argues that through postdigital aesthetics, technology makers can embrace materiality and the inherent qualities of digital technology to formulate a critique of existing trajectories in digital transformation, with consequences for a more sustainable future.