This paper envisions a future in which humans begin to entrust interconnected and intelligent devices and machines with the power to make purchasing decisions on their behalf. Artificial Intelligence (AI), together with the Internet of Things (IoT) and blockchain technology, will likely make this possible. What might be the role of trademarks and the law governing their protection in such a future? This paper responds to this question by considering how the use of AI, IoT, and blockchain technology in the retail space will impact the foundational concepts underpinning trademark law. The discussion highlights the difficulty of shifting trademark law away from its human-centric focus, where core doctrines and principles revolve around human interaction and perceptions, towards a system capable of adapting to a future where devices and machines interact with trademarks. Perhaps the time is ripe for legislative innovation in the field of trademarks.