The aim of this qualitative study is to investigate how teachers and students perceive vocational orientation in the English subject in upper secondary school. The study is based on semi-structured interviews with nine vocational students, three teachers who teach English at vocational education programs and observations of three English classes. The study examines the needs of, and the challenges teachers and students face in the implementation of vocational orientation in the teaching. The starting point of the study is the FYR-project and its objective to improve vocational orientation and the relevance of the common core subjects in vocational education programs. The findings show that both students and teachers are positive towards vocational orientation, but that they experience a number of problems in its implementation. For students, the problem is primarily that the vocational orientation is not perceived as authentic. They find that the vocational orientation they have had in English does not always match the expectations they have for their future jobs. The vocational orientation is therefore of little relevance to the students. For the teachers, there are two main problems with vocational orientation. First, the teachers find that they do not have sufficient competence in the students’ specializations to make their teaching authentic, a finding that matches the students’ experiences. In addition, their school made no attempts to improve the vocational competence of the teachers through courses, or by letting them build experience by teaching the same program over several years. Next, conflicting goals in the vocational education undermine the implementation of vocational orientation. Central parts of the English subject, such as the written exam, do not include vocational orientation. In this way, teaching must focus on a more general vocational competence, instead of being tailored to each profession. To sum up, the teachers' lack of vocational competence and the contradictory goals they are expected to follow results in a vocational orientation that has little relevance for the students. This study ends by discussing issues important for the successful implementation of vocational orientation and the FYR initiative.