Oregon’s PathwayOregon program is opening doors for students who experienced homelessness after the state’s tuition waiver policies helped cover initial tuition and related costs—yet also revealed gaps when students fail required classes. A University of Oregon student described how failing two early classes created a bill the scholarship wouldn’t cover for repeat coursework. The report details how the waiver can protect access during the critical first year, even as repeating courses can expose financial vulnerability for students with unstable housing histories. It also reflects the broader affordability challenge for students who need course completion supports to avoid spiraling costs. Officials and advocates are using these cases to push colleges to align waiver coverage with retention and repeat-course realities, particularly for students navigating academic setbacks alongside basic needs. The update matters for institutional financial aid design because scholarship rules that work for first-enrollment can still fail to keep students enrolled through academic recovery.