The increasing investment in technology for training and learning in organizations underscores the fundamental importance for researchers to understand and investigate technology-mediated learning (TML). Currently, a great deal of Information Systems (IS) training for both IS professionals and end-users has a TML component. With the continuing growth of TML and advances in information technology, there will be a likely increate in TML-based IS training in the future. Advances in technology have created opportunities to deliver mass training as well as to personalize learning. To facilitate understanding in this area, this research analyzes the impact of individual differences on end-user training (EUT) in a TML environment. Using Adaptive Structuration Theory (AST), the learning process is modeled as the appropriation of a training method. Individual differences, or internal structures, are argued to have a significant direct effect on training outcomes and to impact the level of faithfulness of appropriation of learning/training method, thus, having an important indirect effect on learning outcomes. In this study, multiple individual differences were investigated in a laboratory experiment. Data was analyzed using SEM. The results of the study provide a vehicle for researchers, both in IS and Education, to better design and develop training methods and technology tools.