The attempt to regulate the use of artificial intelligence within the public administration (which marks a new phase of public digitization, that of artificial administration) passes through the “resource” of administrative transparency. The essay analyses how the issue has been dealt with by Italian jurisprudence and legislation, also paying attention to the European framework being defined. Transparency is called upon to adapt to the new context, but the technological phenomenon also calls for a rethinking and reshaping of citizens’ levels of legal protection. The challenge, on which the essay reflects, is to maintain adequate levels of guarantee and protection, in a scenario where the old rules risk, however, not being able to govern the phenomenon. The new principles, of jurisprudential formation, now codified by the new Italian “contract code”, propose possible paths of solution, but also challenges and risks of retreat in the protection of rights. The work therefore questions what transparency is necessary and what transparency is possible.