This paper identifies and discusses various challenges met by apprentices when joining the workplace at the very beginning of their training programme. These challenges have become of interest to policy makers and vocational researchers in a context where transitions from school to work are often seen as problematic experiences with growing numbers of young people dropping out of apprenticeship programmes. In a case study drawn from empirical data referring to the Swiss vocational education system, difficulties in sharing meaning at various levels and in (re)negotiating participation at work are described as typical patterns of interactions between apprentices and expert coworkers who train them. These challenges, it is proposed, are not external to language use, but are deeply mediated by discourse practices, including a variety of semiotic resources. From that standpoint, concepts and methods developed in the field of applied linguistics can be seen as relevant tools for illuminating the complexities associated with workplace learning. The paper explores possible continuities and complementarities between vocational education research and discourse studies and argues for an increased research effort in this field of applied linguistics.