Introduction: When considering future learning environments in formal, non-formal, and informal domains, it is crucial to acknowledge the influence of the infosphere in which we are deeply immersed. Methodology: This study is focused on the concept of "circularity" between theory and empirical research. It uses a combination of research methods to carry out an exploratory and comparative analysis among six case studies/universities from five European countries. The analysis takes a multi-perspective approach and applies the translation model to study the complex translation process in supranational, national, and local policy practices. Results: The research highlighted the similarities and differences between the analyzed cases, and subsequently provided valuable recommendations for political decision-makers and academic institutions to guide the digital transition. Conclusions: From the analysis of dimensions, it is clear that the university system needs to reassess its teaching methods, organizational structures, management strategies, assessment processes, relationships, and competence frameworks in the teaching and learning processes. Discussion: This process can be enhanced by exploring new research paths to propose guidelines and direct political planning, organizational strategies, and teaching practices in the future European Higher Education space.