The School 4.0 Plan, promoter of a learning ecosystem formed by the intersection of physical spaces, schedules, activities, tools and human interactions, places a tangible space alongside a non-place produced by the society of surmodernity. The article, building on M. Scriven's (1991) reflection in understanding assessment as a facilitative tool of disciplinary knowledge, grasps the need to empower pupils to become managers of their own learning in an “onlife” context empowered by Artificial Intelligence. The digital curriculum becomes the new frontier for experimenting with innovative forms of measuring the effectiveness of education and renewed quantitative and qualitative indicators for assessing the educational success of students and educational programs. Starting from these premises, the main strategies for evaluating school learning will be studied, with particular reference to the results of the OECD Report "Education at a Glance 2023" presented by the Minister of Education and Merit on September 12, 2023, in correlation with PNRR investments to innovate evaluation processes in the Italian school system. Finally, special attention will be paid to the complexities and peculiarities that characterize the entire School organization (Arduini, G., 2021).