In academic continuing education, the transfer of learning from an academic setting to the workplace is critical. Current research on transfer of training has focused less on the situative determinants for such transfer, and how these are construed by the learner. We assume an actor-oriented perspective on transfer for investigating the individual pathways of what and how professional learners transfer between contexts. Using the lens of self-directed learning, the paper sheds light on the support useful in this process. We conducted a design-based research project, in which we created and implemented a learning design for a continuing education course with a specific focus on learning transfer. We then interviewed a cohort of students on their transfer experience 8 months after the course to understand what the students were transferring, evaluate the support provided during the course and detect opportunities for further support. Results indicated that it was important to establish structures that bridge the academic and work contexts, and prompt reflection and interaction. We discuss the opportunities for further support, especially improving possibilities for personalised feedback.