Changes in working life require development in vocational education and training (VET) to retain industrial currency. VET teachers are key actors in VET, and their continuing professional development (CPD) in vocational subjects is central to the currency of VET. This study is situated in Sweden, with a mainly school-based VET system where VET teachers have the main responsibility for students’ school-based and workplace learning, and they typically have a background in an initial occupation which they now teach their students. The study applies a situated learning perspective, with a particular focus on boundary processes between VET schools and working life, and how the modes of identification of engagement, imagination, and alignment are enacted and influence the identity formation and CPD of VET teachers. The findings are based on interviews with 30 Swedish VET teachers. The qualitative study shows how different forms of boundary encounter between VET teachers and working life, brokering of occupational knowledge, and reconstruction of occupational practices at schools provide opportunities for teachers’ CPD and influencing vocational teaching. It is important for the quality of VET teachers’ CPD to include and integrate the different modes of identification, to allow for updating of different aspects of the occupational identity.