Oregon’s PathwayOregon scholarship model faces high-stakes consequences when homelessness intersects with course failures. A University of Oregon student described how failing two classes as a freshman triggered tuition charges not covered by the scholarship because repeat-course coverage was limited. The report describes how a tuition waiver is opening doors for hundreds of Oregon students who experienced homelessness, reversing the pattern where academic setbacks can permanently derail degree progress due to repeat limitations. For higher education institutions, the story is a reminder that scholarship design details—especially rules around repeats, attendance, and grade thresholds—can create unintended stop-outs and financial instability. The development also highlights the operational need to align student success supports with scholarship policies, so students with housing insecurity can recover academically without cascading financial penalties.