Apprenticeships models are the cornerstone of learning in the medical profession for centuries now. Although we know that apprenticeships are effective in medical workplaces, its precise mechanisms remain tacit and implicit. However, decreasing exposure to relevant learning experiences forces us to develop an understanding of teaching and learning in apprenticeships. Central to the learning in apprenticeships are entrustment of autonomy and supply of expertise by the supervisors. Supervisors perform risk-assessments to estimate how much autonomy can be entrusted to their residents continuously. Such assessments are particular challenging to supervisors when the margins for error are narrow, for instance during complex tasks of surgical procedures. In this perspective we present our insights regarding the teaching and learning during surgical procedures. We demonstrate how supervisors and residents can apply insights in teaching and learning to optimize the learning process during complex tasks.