Educators are simultaneously bombarded with both calls to integrate technology in meaningful ways into their teaching and to promote more student-centered activities which combine both content learning and higher-order thinking. This is no small task given the range of student abilities and interests, the increasing emphasis on state standards and testing, and the persistent challenges regarding reliability and ubiquitous access to the necessary technologies in the classroom. In this study, the authors attempt to work towards a research-based model to connect student-centered technology pedagogy that teachers can effectively replicate in the classroom. They came to this project as educational technologists hoping to find success in leading fifth-grade students to create short, historical, documentary films using the critical eye of a researcher attuned to the classroom teacher perspective. As the title of this article suggests, the authors encountered formidable challenges at nearly every step of the process. The purpose of this article is to honestly document the promising outcomes of an historical documentary project, highlight the challenges encountered, and provide suggestions for future implementation. Specifically, the authors sought answers to the following research questions: (1) To what degree does this historical documentary project support the existing standards-based curriculum?; (2) From the teacher\u27s perspective, to what extent do the technologies employed both support and hinder the educational goals of the project?; and (3) In what ways does this type of student-centered historical documentary project complement or contradict the teacher\u27s predominant pedagogy? For this research study, the authors employed a case study approach using the constant comparative method for data analysis. This approach to framing the study, data collection and analysis, and presentation of findings allowed the authors to closely examine the context and dynamics of the intervention. In two fifth-grade social studies classrooms in Kentucky, students took part in a two week project to create three-five minute historical documentary films. It was found that while the teacher was pleased with the students\u27 work during and at the conclusion of the project, the authors identified formidable challenges in making time for and connecting the content of the project with the local curriculum standards, navigating the challenges encountered with the technology involved, and managing the instructional components of the project in the classroom