This paper reports about a national research project that addresses the question of whether and how digital technologies (e.g. blogs, wikis, headband cameras and mo-bile phones) can help to bridge the gap between the different learning locations in the dual Swiss VET system. Besides socio-cultural activity theory, the project is, inter alia, informed by cognitive psychology of multimedia design. In a series of experimental field studies which involved about 700 apprentices from different professions so far, we tested and evaluated the usability and effectiveness of specifically developed tasks and learning scenarios that use these technologies to document appren-tices’ workplace experiences, and thus make them accessible for further exploitation and reflection within learning activities at school. Moreover, we explored the potential of tangible user interfaces (i.e. physical objects used to control and interact with the computer) to support learning and understanding of complex decision processes and theoretical concepts. In our presentation, we aim (1) to delineate the main idea of the project, (2) to outline and illustrate the rationale for the instructional designs, and (3) to present and discuss exemplary results of the empirical trials.