The First Fleet Convict Database has had a 20 year journey as an exemplar of educational software, published first on mainframe, then microcomputer, and now the web. We describe how the nature of the web environment has changed the nature of this educational package. Pedagogically, databases of primary source data provide students with a learning experience based on the inquiry learning model however, observations of students and teachers in the past 20 years have indicated that database searching is shallow and investigation perfunctory. Before, we could have blamed unwieldy search engines. Now that this obstacle appears to have been removed, we are evaluating whether we have achieved our educational goal of improving students’ research skills. Other pedagogical strategies have been added to that of the database strategy, for example a discussion forum to enable learners to publish and debate their opinions on history. However our statistics show that the forum is the least used part of the site. Although this in part can be solved via classroom teaching, we have added another pedagogical strategy to complement the others. Online role play engages students in developing an understanding of the lives of others and hopefully encourages discussion about the content of the supporting database.