Students in vocational education in Norway take a compulsory mathematics course in the first year of their programme. This course offers opportunities for engaging with mathematics which can be highly relevant to practice in many workplaces. Working with vocationally connected mathematics tasks, tasks designed to draw on students’ future working contexts, is one way of trying to connect to students’ possible future vocations. This study aims to understand how students interact with such tasks with a particular emphasis on the roles of norms, authenticity and students’ positioning between the practices of school, the workplace and everyday life. In this study, I observed students working with specially designed vocationally connected mathematics tasks in three different vocational education programmes in Norway: Design and Crafts, Media and Communication, and Technical and Industrial Production. The data comprise of video recordings and field notes of the students’ interaction with the tasks. Grounded in a socio-cultural approach, with an emphasis on students as participants in multiple communities of practice, the analysis is framed in the theoretical concepts of norms, authenticity and boundary object representations. Working from the starting point that the students are experienced as participants in mathematical classrooms but are still newcomers in their future vocational practice, the analysis concentrates on enacted norms in the classroom and references to out-of-school routines, knowledge and practices.