Nowadays, many individual and team training trajectories include multiple simulators and training environments that differ in functionality, appearance and interface from each other and from the working environment. The use of different training environments within one training trajectory requires from students the transfer of knowledge and skills learned from one learning situation to a 'new' (learning or working) situation. This paper discusses a research study aimed at identifying transfer problems between generic and type-specific simulators for the RNLN Operational School. Using a combination of qualitative and experimental research methods, this study shows that there are many factors contributing to the large relapse students experience when moving from generic to type-specific simulators. Recommendations include, amongst others, a change in training strategy and a different design and organization of the training trajectory.