What does it mean for a community writing assistance program to bridge the gap between the university and the community? What makes for a successful alliance between these two worlds usually considered distinct? Our paper addresses these questions by reflecting on the factors that have contributed to the growing success of our CWA program at the University of Wisconsin-Madison. Taking into account the varied alliances forged through our work — between the funding organization, instructors, community leaders, and writers themselves — we hope to offer a multi-faceted picture of local literacy outreach and partnership.