The increased popularity of desktop documentary making among both teachers and students in history classrooms warrants an examination of its integration into classroom instruction. This multiple case study focused on two secondary students in an AP European History course during a unit that featured desktop documentary making. Employing Cultural Historical Activity Theory (CHAT) as a theoretical framework, this study revealed that the students constructed historical narratives with multiple web-based encounters that affected their composition over a span of time. Whenever students experienced tensions in their narrative process, the students made historical judgments that furthered the narrative process. These judgments were, at times, based on evidence, and at other times devoid of evidence. These findings suggest that students may form baseless historical conclusions when given creative freedom in a desktop documentary making assignment. The challenge for history teachers and teacher educators who seek to integrate desktop documentary making into their instructional repertoire is to balance the need to provide students with creative freedom while creating an instructional setting that effectively and efficiently addresses students' historical understanding. (Contains 3 figures and 1 table.)