In contemporary society, knowledge plays a key role in professionalism and in interpersonal relations. The profile of the future citizen must be rethought with the intention of providing expendable knowledge to use in work environment, but also in terms of flexibility in lifelong learning, adapting people to the mutable needs of today’s labor market. Then, the learning evaluation will be thought in relation to this new goals, since the assessment of learning outcomes is a fundamental part of the training process, the phase of the critical reflection, the rethinking of the intervention designed and implemented. The traditional approach to evaluation consists in a systematic process of collecting and interpreting data, in which emission of a judgment does not consist in a mere sum of the data found in the measurement phase, but is characterized by the interpretation of the same, with respect to the criteria established and respect to the purposes for which it was decided to measure and evaluate. In the last two decades, the emphasis has placed on new evaluation methods that were able to support learning outcomes in a systematic way, with attention not only to the quality of knowledge acquired, but also to cognitive processes and meta-reflection's strategies involved. It talks about authentic assessment as it aims to facilitate social, cognitive and metacognitive learning, able to encourage students to mobilize their knowledge in real tasks that are close to the contexts of everyday life. Nowadays, the evaluation is considered intrinsic action to the educational process, and is central to the debate on the quality of education because it is necessary to promote not only the expression of rating scales, but, also and especially, the promotion of meaningful learning processes. This paper will aim to clarify what is authentic assessment, what are its contexts of use and will offer concrete examples to describe a possible path that can help to improve assessment practices. The construction of authentic tasks, in fact, provides for the standards and criteria definition to clarify the performance nature, and to communicate the complete description of the final task in terms of expected and desired results, in order to encourage the development of metacognitive regulation processes. This contribution, also, clarifies the circumstances in which the student's competences and his subjective attribution of meaning to the task is revealed through a simulation of situations-problem. The evaluation action, in this way, highlights the value and significance of the training process with respect to each student, encouraging him to mobilize their knowledge/experiences to identify an appropriate solution to the tasks required not only in school but also in real life.