Today’s Education is increasingly mediated by digital technologies that imply new challenges that need to be addressed in detail to turn them into opportunities for advancement and evolution. Such is the case of the use of artificial intelligence in learning assessment processes, which is forcing us to rethink traditional methods, mechanisms, and strategies to assess student learning achievement, especially in distance and online Education. Given the complexity of the above, this analytical essay proposes a look at artificial intelligence developments that support the so-called “evaluation 4.0”, based on the application of fuzzy logic, homeostasis, and the cybernetics of self-regulation. Such an application would provide technical support and a general understanding framework for the evaluation processes for both teachers and students to promote evaluation processes more in line with the flexible and often imprecise and ambiguous nature of the learning and performance associated with the skills assessment in the framework of the fourth industrial revolution.