Growing numbers of liberal arts colleges are creating collaborative digital scholarship projects. Defining the roles of faculty, student, and web developer in the semi-hierarchical world of liberal arts colleges—where pedagogical goals must be constantly kept in mind—can be tricky; however, doing so is critical to the long-term success of such projects. Drupal, an open source content management system, enters this space at a crucial moment, allowing a new level of collaboration in the creation and maintenance of sites by web developers, faculty content providers, and all student assistants. Getting the work flow right while keeping the experience rewarding for all concerned is one key to sustainability. In this seminar, members of the team behind the text annotation site Dickinson College Commentaries (faculty director, web developer, and students) discuss the problems, pitfalls, and opportunities of collaborating with Drupal in a liberal arts context.