Many minority, first-generation, and low-income students aspire to college; however, the college application process can present a significant obstacle. These students cannot always rely on their parents for college information and must instead turn to their high schools, where counselors are in a key position. Drawing on a two-year field study at two racially and socioeconomically diverse high schools and interviews with 89 students and 22 school counseling faculty and staff, I examine the role of trust in creating successful student-counselor relationships that can facilitate the transmission of social capital during the college application process. My findings indicate that distrust between counselors and students is due to a lack of shared understanding regarding expectations and roles. My evidence suggests that the diverse nature of the school context created structural constraints that contributed to this distrust. By analyzing the strategies of one counselor who succeeded in connecting with students and working through these structures, I demonstrate ways that trusting relationships can be formed.