This article details the evolution and results of a service-learning project designed to extend cross-cultural relationships via online social networking between students at a U.S. Bureau of Indian Education boarding school and teacher candidates in a required diversity course. The goals for the partnership included helping Native American students identify personal strengths through mentoring relationships, and encouraging teacher education candidates to develop their intercultural communication skills. We assessed the project using qualitative and quantitative measures: identification of significant themes emerging from teacher candidates' reflections; comparison of recurring reflection themes to stages of Bennett's Developmental Model of Intercultural Sensitivity; and statistical analysis of candidate responses on Cushner's Inventory of Cross-Cultural Sensitivity. The analysis reveals challenges and opportunities for student and candidate learning and stimulates questions that shape future directions for service-learning in an increasingly digitized world.