This paper analyzes the effects of the helicopter dynamics on pilots' learning process and transfer of learned skills during autorotation training. A quasi-transfer-of-training experiment was performed with 10 experienced helicopter pilots in the SIMONA moving-base flight simulator at Delft University of Technology. Pilots had to control an in-house flight dynamics model setup to simulate two types of helicopter dynamics: (1) a "hard"dynamics characterized by a low autorotative flare index requiring high pilot control compensation and (2) a "easy"dynamics characterized by a high autorotative flare index with low pilot control compensation required. Two groups of pilots tested these types of dynamics in a different training sequence: hard-easy-hard (HEH group) and easy-hard-easy (EHE group). The main conclusion of this study proved that simulator training for autorotation can best start with pilots training in the most resource demanding condition. A more challenging helicopter's dynamics will require higher pilot agility and more rapid responses to his/her perceptual changes. This will result in pilots developing more robust and adaptable flying skills. Indeed, a clear positive transfer of training effect was observed in the experiment presented in this paper in terms of acquired pilot skills in the HEH group, but not the EHE group. Positive transfer was especially observed in terms of reduced rate of descent at touchdown. The two groups differed in the control strategy applied, with the HEH group having developed a control technique mimicking more closely the one adopted in a real helicopter.