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. The online version of the First Fleet Database has removed this obstacle, but students’ research skills still appear to be limited. 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 by the way the teacher sets up the class dynamics, we have added online role play as another pedagogical strategy to complement the others. Hopefully the role play will lead students into deeper searching of the database as they become more engaged in developing an understanding of the lives of others. The role play has been used with two online classes in different contexts in the past year. The evaluations from these classes suggest recommendations about the key role of moderator/s; effects of non-participation; connecting character descriptions to the learning outcomes; and preparation of kick-start scenarios to follow the kick-off scenario. All of the above impact on the design of role plays in general in other topic areas, especially if the role play is to be made transferable to other teachers.