This chapter presents an extended critique of the Quoine case in Singapore where the seven trades at issue were fully automated. The central point of the case is that one or both contracting parties decided to deploy or rely on technological assistance and that does not in itself justify a departure or a deviation from long-standing legal principles of contract law. While there is no denying that the contracting process can be optimized by means of a broad range of technologies of varying complexity and that such technologies often create unique risks, it does not follow that such technologies have a disruptive effect on contract law itself. Innovation in commercial dealings need not lead to an innovation in contract law. To the contrary, the latter has shown a surprising resilience to technological disruption, mainly due to the broad, flexible, and technology neutral formulation of its core principles.