In this session, participants will share ideas, challenges (either anticipated or experienced), and best practices for engaging students as scholar-collaborators in digital projects that extend beyond the classroom. We will discuss digital projects that hinge on collaboration between classrooms and community partners such as non-profit organizations, archives, and libraries. Such collaboration can provide valuable opportunities for undergraduates to conduct research and build digital literacies while advancing the mission of community and library partners by, for example, enhancing access to digital archival collections. However, such collaborations require careful planning and execution to ensure relevance for everyone involved. Whether you have led or contributed to a digital classroom collaboration with a community partner, or are interested in potentially doing so in the future, this session will provide an opportunity to pose questions and share expertise, experience, and considerations for planning and assessment. Local faculty and instructor participants are encouraged to invite undergraduates they have supervised on digital classroom projects to contribute to the discussion about the benefits and challenges of undergraduate participation in collaborative, community-engaged digital projects.