Artificial Intelligence (AI) started to impact many facets of the economy and of citizens’ routine activities. This article contributes to our understanding of how the legal system is reacting to the ongoing uptake of AI and the disputes or right infringements this might create. Select legal cases regarding the use of AI technology for automated decisions are reviewed, with a focus on filings in Europe and the United States. This exercise reveals which type of legal challenges can be expected when it comes to deploying automated systems in these jurisdictions. Additionally, incipient regulatory efforts targeting AI on both sides of the North Atlantic are introduced and briefly discussed. The paper sheds light on how different legal systems accommodate an emerging technology with disruptive potential and offers a mapping of exemplary legal risks for prospective actors or organizations seeking to develop and deploy AI.