The presence of intelligence and rationality in Artificial Intelligence and the Internet requires a new context of analysis in which Herbert Simon’s approach to the sciences of the artificial is surpassed in order to grasp the role of information in our contemporary setting. This new framework requires taking into account some relevant aspects. In the historical endeavor of building up AI and the Internet, minds and machines have interacted over the years and in many ways through the interrelation between scientific (...) creativity and technological innovation. Philosophically, minds and machines can have epistemological, methodological and ontological differences, which are based on the distinct configuration of human intelligence and artificial intelligence. Their comparison with rationality and its various forms is particularly relevant. Scientifically, AI and the Internet belong to the sciences of the artificial, because they work on designs that search for specific aims, following selected processes in order to achieve expected results. Technologically, AI and the Internet require the support of information and communication technologies. These have an instrumental role regarding the existence of AI and the Internet. Also ICT shape their diverse forms of configuration over the years.Within this framework, this paper offers a new context of analysis that goes beyond Simon’s and follows four main steps: the interaction between scientific creativity and technological innovation as the philosophico-methodological setting for Artificial Intelligence and the Internet; artificial intelligence and human intelligence as epistemological basis for machines and minds, where the differences between artificial intelligence and human intelligence are made explicit and the analysis of minds and machines is made from the perspective of rationality ; intention and its difference with design of machine learning are considered to distinguish human intelligence from artificial intelligence; and the internal and external aspects of artificial designs in contemporary society are considered through the perspective of rationality, which leads to the transition from intelligence to rationality in the Internet as well as to the historicity of information. (shrink)