Challenging students to create digital documentary films in history courses engages students in both mastery of content knowledge and higher order thinking experiences. Teachers considering this type of work must contend with the focus on standards- based testing, a wide breadth of content to be covered, the challenge of finding relevant primary source materials, and restrictions related to copyright and Fair Use. This paper explores a resource site for teachers, Digital Docs in a Box, that attempts to mediate some of these concerns and support their students in the creation of digital documentaries. First, we explore the rationale for student creation of digital media, the challenges inherent in these endeavors, and the creation of the resource site. We then overview the structure and use of the site, with an illustration of how a practicing teacher would use one of the documentary kits in the classroom.