Purpose: By examining data from interviews with students in the Upward Bound (UB) Program (a federally sponsored program that provides academic support to students at risk preparing for college entrance), this study seeks to strengthen understanding of the stages of trust in educational organizations that serve urban youth and in so doing provoke further thought regarding our collective understanding of trusting dispositions and behaviors in educational organizations. Research Design: This qualitative piece uses data from a study of student participation in leadership and interviews, observations, and document analysis of participants and informants to build conceptual understanding of the stages of interpersonal trust in educational organizations. Participants included 20 recent high school graduates enrolled in the summer Bridge Program of the UB Program at a university in a midsized city. Findings: Better understanding of the stages of trust came from examining the concept in an educational organization that serves urban youth. Students described their move from calculation, to courtship, and finally to contribution in terms of taking and giving behaviors as they interacted with UB staff and administrators. Conclusions: This study highlights the following as implications and areas for future research and practice: First, study participants provided information that complicates the concept of trust in educational organizations that serve urban youth. Second, study data highlight how trusting relationships develop as individuals test others' capacity to act for their benefit. Further studies that explore these relationships are encouraged. Third, study data imply that educational organizations play the initial role as giver in give-and-take relationships that characterize trust among urban youth. Further research is needed to understand whether and why this is so. Finally, issues of gender and race were not explored at length in this study. Deeper examination of the interplay of trust, gender, and race may help explain this study's findings and provide insight into trusting dispositions and behaviors among urban youth. (Contains 1 table and 1 figure.)