This study aims to investigate the Swiss initial vocational education and training (IVET) partnership from the perspective of several stakeholders on the ground. Collaboration between stakeholders is essential in dual IVET to connect school- and workplace-based learning and to ensure the quality of the entire system. However, such collaboration can be challenging, given the different epistemic natures of the school and the training company. Apprentices, that regularly cross the boundaries of vocational school and training company, often struggle to connect the learnings that they have acquired from both places. Adopting a boundary crossing perspective, we explore perceptions of IVET partnership in terms of challenges and learning opportunities for the stakeholders on the ground. We realized focus groups with apprentices, vocational teachers, and in-company trainers (N = 64) from several professional fields. The data were analyzed in an inductive and deductive manner, using a thematic analysis. The main results highlight that the participants consider the collaboration between stakeholders to be weak: the links between schools and training companies appear to be scarce and not supported by explicit or formal strategies. Further, the apprentices act as brokers, but they are often not supported in connecting school- and workplace-based learning. These results can provide new insights into how the IVET partnership could be designed.