This chapter outlines a comprehensive guide to the creation of a fruitful learning environment for simulation exercises. In this respect, the role and importance of monitoring students’ ongoing activities during simulations is highlighted as the basis of being able to support the students in their learning processes. In addition, the chapter outlines how role-plays in the simulated environment can function as an arena for professional learning, using the threshold concept framework to illustrate the messy, non-linear process of becoming a seafarer.