Artificial Intelligence, AI, can be of great use in the anthropization processes of the territory and urban centers. For many years, territorial planners and urban planners have been calling for the creation of Observatories to follow, evaluate choices and implementations. What Kevin Roose reports in the 2023 article in the New York Times about conversations with AI devices is astonishing [18]. Although several of the chatbot’s statements and responses present some inconsistencies and could be a free association—but with internal coherence—of the billions of data, of a multidisciplinary nature. Of this we have no proof of the opposite nor of the correctness of this sentence except through “human” verification. With AI there is the possibility of making a sort of increasingly larger virtual reproduction of what is observed. That is, the holistic approach can be increasingly approached. And this allows the construction of increasingly complex and “complete” scenarios. But precisely because of the methods of building AI, i.e. feeding it with “data” which are in any case “phenomenal” even if translated into quantitative and/or qualitative indicators, it is still a “partial” action both from a territorial perspective both environmental and social. Action which in fact, in relation to these aspects, risks being “conservative” of the status quo. Therefore, the writing highlights these aspects, potential and limitations in order to provide the most operational indications possible.