Background/Context: In the field of education, the lens of agency has provided a valuable conceptual alternative to deterministic portrayals of schools as oppressive institutions where teachers and students have little power over the conditions in which they teach and learn. A number of studies have investigated teacher and student agency, but few have explored the relationships between the two, particularly in regard to how teacher and student agency relate in high-need and high-diversity contexts with exemplary student graduation outcomes. Purpose/Focus of the Study: In an effort to address the paucity of research investigating the relationships of teacher and student agency, this analysis draws on seven qualitative case studies of secondary schools achieving a trend of above-predicted (i.e., odds-beating) graduation outcomes. We pursued the overarching research question: What are the relationships between teacher and student agency in odds-beating schools? Setting: The study took place in a purposeful sample of odds-beating secondary schools identified through multiple regression analyses. The sample included schools in rural, suburban, and more urban communities and were distributed across various geographic regions in the state of New York. All schools shared a pattern of above-predicted graduation outcomes, taking into account student demographic factors (percentage of students economically disadvantaged, African American/Black, Hispanic/Latinx, and English language learners). All schools met the criteria of being within the normal range for wealth ratio as well. Research Design: This qualitative multiple case study focused on data generated from interviews and focus groups with 302 participants, including teachers, student support specialists, and school and district leaders, as well as field notes gathered during guided school tours, and documents. These data were analyzed using qualitative comparative analysis methods in multiple phases of deductive and inductive coding. Conclusions: Study findings indicate that when teachers are offered opportunities to act as agents, they tend to offer opportunities to their students similarly. This research also suggests that affordances for teachers to assert agency can mitigate the constraining effects of state accountability system compliance-oriented practices. We conclude that teacher and student reciprocal agency merits further study and offers theoretical insights of particular import in high-needs and high-diversity school contexts.