This article reports on a research project in which a digitally based assessment model is being developed for the Pacesetter Program. This program, established by the College Board to prepare culturally diverse students for higher education, is built around a curriculum that reflects not only the world that these students come from but also the rapidly evolving technological society that they are expected to participate in. The assessment model is being developed for an English language arts course, in which students work with culturally diverse material in three domains: print literacy, film literacy, and media literacy. At the heart of the model are three tasks: a planning task that requires students to focus on factual content, an interpretation task that requires them to make sense of that content, and an application task that requires them to deal with the content in a broader context. The students use digital tools to carry out these three tasks: For example, they use a graphic organizer in the planning task to gather information that will be useful as they perform the higher level tasks that follow. As an illustration of how this model works, the article presents an assessment activity built around the ways in which the media have presented the results of Census 2000 with respect to cultural diversity.