Background: A significant factor of clinicians’ learning is based on their ability to effectively transfer acquired knowledge, skills, and attitudes from specialty-specific clinical courses to their working environment. Material and method: We conducted semi-structured interviews with 20 anaesthesiologist trainees (i.e. residents) in four group and five individual interviews using SRL principles as sensitizing concepts. Data were collected and analyzed iteratively using thematic analysis. Results: Advanced trainees are highly motivated to explore what they have learned in specialty-specific courses, but they often face several barriers in implementing their learning in the workplace environment. Four themes emerged from the interview data: ’Be ready to learn’, “Take the ‘take-home-messages’ home’, “Be ready to create your own opportunities’, and “Face it, it’s not entirely up to you’. Understanding the challenges regarding transferring knowledge from courses to the working environment is an important lesson for assisting trainees set their learning goals, monitor their progress, and re-evaluate their SRL processes. Conclusion: Even for advanced trainees, successfully transferring knowledge from specialty-specific courses often requires adequate commitment and support. Medical supervisors and other relevant stakeholders must be aware of their shared responsibility for creating individual environments that support opportunities for trainees to self-regulate their learning.