This interpretive case study explores how multiple layers of federal and local policy and practice converge in a local iteration of a federally-funded and regulated college access program, Upward Bound, and are reflected in employees' constructions of the identities of student and family participants. The study further investigates the relationship between program-sanctioned and employee-constructed understandings of participants, and the planning and implementation of a series of routine interactions with them, in the form of case studies of two classes implemented with students as a major program activity. Finally, the study questions how two program participants with memberships in multiple underrepresented groups—a Latino first generation United States citizen identified with a disability who receives special education services, and a Latina immigrant who participated in English Language Acquisition programming—constructed notions of what it means to be a college student, including how these notions reflect their participation and the content they were exposed to in Upward Bound. Findings show that federal program policy overwhelmingly constructed participants in deficit-laden ways, most often in connection with their background and that these constructions were reflected in program-level constructions of participants, as well. However, there was ambivalence over the construction of students' identities, and the goals of program participation at the local program level, which carried over into the way that teaching and learning was organized in routine interactions with participants. While some forms of participation in the two classes animated students as passive learners of discrete academic skills, others built students' critical consciousness as members of nondominant groups. Further, students were positioned in contradictory ways that included notions of demonstrating both academic need and academic capacity. Federal policy also ignored race, ethnicity, and disability, despite overwhelming statistics that nondominant racial, ethnic, linguistic, and ability groups are underrepresented in college. These silences were reflected at the local program level, as well, especially in relation to students identified with disabilities. These silences, along with the particular forms of participation experienced appeared to influence a disidentification with the academic nature of schooling of the student participant identified with a disability, while the other student demonstrated ambivalence around college-related decisions, perhaps in connection with some of the contradictory identity work she participated in within the Upward Bound class.