The purpose of this article is to review a partnership between a teacher education department and a dropout prevention program. The partnership developed from a variety of communities' needs, no less of which was that of reconnecting marginalized youth at a local dropout prevention school with their community through cultural and civic exploration. At the heart of the relationship was the building of powerful curricular experiences for these students through the support of preservice teachers who mentored the at-risk youth. The CREATE project (Cultural Reflection About Evansville--Art Transforms and Engages) was an interdisciplinary experience that supported the development of a strong service-learning environment. Developing civic literacy with participants was a tricky business as faculty, students, and community partners explored ways of revitalizing a downtown area. Some challenges were anticipated; others were unique to the project. However, a few concerns have greater implications for higher education professionals and community partners as they develop a service-learning curriculum.