Users at all levels of expertise prefer to learn software tools by exploration. However, our knowledge of how users explore system, and how exploration can lead to effective learning, remains limited. In this work studies are made of learning by exploration looking at factors that lead to retention as measured by the time saved in performing similar tasks repeatedly and for different task instructions intended to promote different modes of exploration. A theoretical model of the cognitive processes involved in exploration is extended to account for the differing patterns of explorations and to model the consequences if the various kinds if exploration for retention,. The results will be incorporated into a software design methodology using the cognitive walkthrough approach for tools that can be effectivelymastered through exploration.