This paper is focused on connectivity and competence development in the dual VET systems of Switzerland and Germany. Besides cultural historical activity theory and its respective conceptualization of school-workplace connectivity as a process of interaction between two different systems of historically-related activities in which learners are simultaneously involved, we adopt a developmental ecological as well as a phenomenographic perspective. In this perspective, we aim to explore challenges and potentialities of the dual VET system as perceived by its key actors: apprentices, teachers and company trainers. In a first attempt to approach this aim, thirty individuals (balanced by role and country) involved in the initial dual VET system in the field of health, business administration, and industry were interviewed on their own experiences, meanings and opinions on school-workplace connectivity. In our presentation, we will pay particular attention to contradictions and discrepancies as they figured out in a content analysis of the interview data. Because of their frequent nomination, we will specifically focus on perceived differences in the meaning of (1) competence development and (2) competence assessment, as witnessed by the interlocutors. (3) Finally, we will discuss, how these meanings could be negotiated in a wider shared endeavour of integrated competence development.