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In this paper, we analyse the structure of evolving moral dilemmas with an eye of regard for the increasing importance of the role of artificial intelligence in such context. Starting with the analysis of the famous trolley problem experiment as formulated by Philippa Foot, we consider subsequent variants of this moral dilemma conceived throughout the years, culminating with formulations of the trolley problem concerning artificial intelligence, in which self-driving vehicles will have to make life or death decisions autonomously. In doing so, we investigate the basis for the construction of dilemmatic questions both for humans and machines by considering the problem from a philosophical, social and neuroscientific perspective. After considering and analysing the trolley problem in utilitarian and deontological terms, we follow Rittel and Webber’s footsteps, by highlighting the fallacies of the deontological and utilitarian traditional ‘one-right-answer’ approach, where a solution is undoubtedly right or wrong, and claim that moral problems are not, due to their intrinsic dilemmatic nature, resolvable. By rejecting an aut-aut approach, we find ourselves contemplating the possibility of neither approach being right in an absolute sense. Given these premises, we present a different approach on the matter, arguing for the central and creative role of the tragic as a new tool for enhancing both human and autonomous vehicles’ approach to moral problems.