The paper studies the establishment of work experience programs in the context of the Greek Higher Education Institutions (HEIs) and connects it with the attempts to include Work-Based Learning (WBL) in the education system on a large scale. Emerging challenges caused by two significant recent changes in the Greek Higher Education landscape set the aim of this study. The integration of Technological Education Institutions in Higher Education Institutions and a significant financial change initiated by the new law which transfers the cost of compensation for traineeships to host institutions and not to Operational Programs. The paper presents the current state of the art in the Greek Higher Education and provides a detailed analysis of the existing barriers. The particular study acquires special interest in light of the intensification of the efforts made all over the world aiming to improve the organization and implementation of such interventions. Work experience programs offered by HEIs are required to be better adjusted to the special educational and labor market characteristics of each country and to become more effective. In Greece, the educational and the labor market policy framework recognizes the significant contribution of WBL in general and of traineeships in particular to the development of the appropriate professional knowledge and competences by higher education students. At the same time, traineeships can operate as a communication channel between educational institutions, businesses and social partners, which facilitates their multifaceted information exchanges. Considering, however, the operational autonomy that has been granted to HEIs in Greece, each University develops its own strategy as regards the connection between higher education studies and the labor market. The research presented in the paper constitutes a quantitative analysis of all the types of traineeships implemented by the Greek HEIs with special reference to certain axes, the optional or mandatory character of WBL, the awarded ECTS, similarities of WBL within the same scientific field in different HEIs, the possibility to undergo a WBL placement abroad.