The high drop-out rate in upper secondary education is a major challenge to European and US educational programmes. Upper secondary education in Norway faces a similar challenge, because in recent decades, around one-third of the students drop out of the educational programmes. The majority of the drop-outs are students in vocational programmes, and a substantial number are apprentices at the workplace. With these high drop-out rates and the ensuing personal, social and economic consequences, it is vital to address how upper secondary education systems can keep students connected throughout the programmes. By thoroughly analyzing learning environments and the experiences, interactions and processes which youth deal with during vocational education, insights into how characteristics of the learning environments relate to dropping-out and connectedness may be brought into educational discussions. The case study presented in this article explores how workplaces constitute learning environments and how apprentices participate in the learning environments of work according to their dispositions, aims and life plans. The findings show that the apprentices had different agencies and that they were involved in two distinct participation patterns at the workplace: a collaborative pattern and an executive pattern. Our findings also suggest that strong agency for the vocation may keep apprentices connected throughout the educational programme, although they are afforded an executive participation pattern. Based on our findings, it is appropriate to raise questions as to whether an unclear agency for the vocation, together with affordance of executive participation patterns, may suggest one possible answer for the high drop-out rate among apprentices. (Contains 1 figure and 1 footnote.)