By examining data from interviews with students in the Upward Bound program (a federally sponsored program that provides academic support to students at risk who are preparing for college entrance), this study seeks to strengthen an understanding of the role of trust among urban youth at risk in the educational organizations that serve them. This work makes a unique contribution to the work of school public relations by highlighting the perspectives of urban students at risk on the role of trust in their educational organization. This qualitative piece uses data from a study of student participation in leadership, and it uses interviews, observations, and document analysis of participants and informants to build an understanding of the role of trust among urban youth at risk in educational organizations. Participants included 20 recent high school graduates enrolled in the summer Bridge Program of Upward Bound at a university in a midsize city. Students provided important insights into the role of trust. Some facets of trust (e.g., benevolence, honesty, openness, reliability, and competence) emerged from the interviews providing empirical support for recent theoretical work on the concept. For students, establishing and maintaining trust with each other, with faculty, and especially with staff members contributed to their decisions to help the Upward Bound program meet its purpose of motivating students to graduate from high school and enter college. Educational administrators in academic support programs and schools whose students benefit from these programs serving urban youth at risk will benefit from making efforts to forge trusting personal relationships with the students, parents, and other community members within students' spheres of influence. Findings from this study suggest that urban students at risk may already view themselves as being capable of working with educational organizations that are willing to share power and flatten hierarchies. By understanding how urban students contribute to trusting relationships, urban school administrators may build their personal capacity to effectively communicate with this group of young people and develop strong ties with the communities whom these youth represent. Finally, the results of this study suggest that building trust among students may serve as a key component in successful school community relations if, as suggested in this work, students actively support and advocate for educational organizations with which they form trusting bonds.