Thanks to ICT, schools were able to reinforce the construction of synergistic collaboration networks with the world of businesses, expanding the training offer of Work Experience Programs (PCTOs) and giving students the possibility to participate in immersive on-the-job experiences which are particularly innovative in terms of their digital components. The reflection on the new features of the academic design of Work Experience Programs, contingent to the differing degrees of digitalization attributable to projects, can be traced back to the research activities carried out by a group of scholars from “La Sapienza” University of Rome within the purview of the Research Project of National Interest (PRIN) “Evaluating the School-Work Alternance: a longitudinal study in Italian upper secondary schools”. The reference empirical base for the analysis comprises 249 Work Experience Programs (AY 2021/2022), directly uploaded by 78 Italian upper-secondary schools – divided into traditional, technical and vocational institutes – onto a digital platform dedicated to the storage of materials. An inspection procedure was set up for the projects' content, structured by keywords, which resulted in the identification of 65 Work Experience Programs, which were then in turn examined to highlight the features and specifics which ultimately allowed for the discernment of first and second level digital content projects. The Work-Experience Programs' digital component was evaluated with respect to the offer of professionalizing experiences, connected with on-offline learning modules, whose prerogative is that of propagating the principal types of literacy associated with the digital. The latter are to be considered social practices located at the center of the didactic training strategy of Work Experience Programs, whose objective is channeling a complex and integrated system of technical, relational and value-based resources, on which the concrete development of digital skills depends.