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Trademark law is quintessentially a response to all-too-human cognitive failures: We have limited time, limited attention spans, limited memory and an ability for pattern recognition that on the one hand is highly evolved, but also prone to manipulation. But what happens as we increasingly outsource our purchasing decisions to machines? Artificial Intelligence (AI) in the form of autonomous intelligent shopping agents (AISA) such as Siri or Alexa continue to gain autonomy. However, two trademarks that would not be confusing for a human may be difficult to distinguish for an AISA, and conversely, an AISA may be able to distinguish trademarks that are confusing for humans. Similarly, actions intended to infringe a competitor trademark may not be triggered when shoppers are AISAs, but now novel forms of trademark infringement may become possible only in the realm of AISAs. This paper discusses whether the advent of AISAs in retail, and the following change in consumer practises, challenges the current international trademark regime, with a particular focus on the WTO Agreement on Trade-Related Aspects of Intellectual Property Rights (TRIPS).