User learning is central to the effective use of information technology within organizations, particularly given the changing nature of IT over the past decades. Research indicates that self-training is the most common means by which users learn. In addition, the use of Web-based training within organizations in these self- directed learning situations is increasing. The purpose of this research is to investigate the increasingly popular self-training phenomenon within organizations by examining the self-regulated learning strategies that individuals use in Web-based training situations, and how they influence learning outcomes. To do this, a two phase study was designed. Phase one of this study has been completed, and phase two has been initiated. Phase one took us into the field to explore interviewees’ self-directed learning experiences by understanding the strategies they used and learning difficulties they encountered. It involved 27 interviews with knowledge- workers from a variety of organizations. Phase two (in progress) provides a field test of the research model. Organizations invest a great deal of resources toward training end users, and this research will assist organizations in gaining a return from this sizable investment in training end users, and in managing their most important resource—knowledge.