The integration of experiential learning with community service is a prevalent pedagogical approach in Library and Information Science (LIS) education, particularly in courses like digital collections and fieldwork experiences. This paper explores the challenges and opportunities associated with community-based digitization projects within an LIS program, drawing upon anecdotal evidence from various instances of faculty and student involvement. Through reflective analysis, the author identifies key themes such as community needs and barriers, the practicality of hands-on learning, and the complexity of collaboration. The paper proposes a framework for potential interinstitutional and cross-community collaboration, aiming to bridge the gap between LIS education and practical applications. By delineating essential resources and potential avenues for support, the framework seeks to facilitate the sustainability and success of community-based digital initiatives. However, uncertainties regarding funding accessibility and institutional policies pose significant challenges, highlighting the need for ongoing research and collaboration in this field.