Conventional definitions of "on-time graduation" and "college readiness" often place the needs of traditionally marginalized students (first-generation, low-income, immigrant and/or students of color) in a deficit light. This multi-case study explores how school leaders at two public high schools are redefining and reframing these policies for their specific student populations. The findings suggest that extending graduation beyond 4 years and using intersectional understandings of college readiness increase traditionally marginalized students' opportunities to finish high school and pursuing postsecondary education.