Transfer of training has not been perceived as successful for training programs in bringing about targeted knowledge, skills, and attitudes (KSA). The review of current literature revealed a lack of consensus of the nature of transfer and ambiguity of the role an individual's attitude plays in the learning and transfer process. To provide insight into trainees' attitude from a holistic view, we conducted a multiple-case study to investigate trainees' learning and transfer experience in depth. The findings from five independent cases revealed high transfer rates of newly acquired KSA to teaching, and that trainees' affective, cognitive, and behavioral attitudes are perceived to be closely related to their learning and transfer. Recommendations of training design practice such as experiential learning design and signature pedagogies across different disciplines are provided based on the training program design and the triangulated data resources.