Analysis of diverse first-year and first-generation learning communities students' reflective narratives shows this population of students at an urban commuter college of technology face significant challenges in the transition into college. Designed to assist in this transition, the "Our Stories" digital writing project incorporates reflective writing in the long established, yet recently revitalized, learning communities program. Through analysis of the "Our Stories" project, we examine how the structure of our learning communities program, together with writing on an open digital platform, builds community and has the potential to positively influence students as they identify, and begin to make sense, of the social, emotional, and bureaucratic challenges in their transition into college. The role of peer mentors, faculty and administrators in this project is discussed.