In the fall of 1996, the Arkansas Archeological Survey and the Department of Foreign Languages at the University of Arkansas, Fayetteville received a $180,000 grant from the National Endowment for the Humanities Teaching With Technology program. The goal of this grant initiative was to encourage creation of content-rich, computer-based materials for teaching history, literature, and languages. The grant team produced a CD-ROM called First Encounters: Native Americans and Europeans in the Mississippi Valley. The CD-ROM was designed to teach students how to critically evaluate differing multicultural perspectives using historical sources. A post-development evaluation of these materials yielded favorable student ratings and successful learning outcomes, however we decided to add a second generation of instructional improvements. The primary goal of this article is to describe the implementation and preliminary evaluation of one of these improvements, a web-based social process experiential simulation prototype called Two Worlds. Two Worlds was designed to enhance critical thinking by engaging users to explore a digital micro-world, participate in role-plays, and construct mind maps through and with collaborative electronic tools.