Race and class are deeply embedded in the way the field and teachers think about linguistic and written performance. Yet, addressing and understanding racial and linguistic prejudice remains important to the fairness of one’s pedagogies, assessment practices, and curricular development. The author argues that social justice approaches to assessment require instructors and program administrators to rethink assessment concepts such as reliability and validity with an eye toward the ways disadvantage is embedded in the very construct task responses and assessment materials used to define quality writing. Because historically Black colleges and universities (HBCUs) present a unique blend of culturally relevant teaching and traditional (i.e., White) definitions of quality writing, they provide a unique site for inquiry into questions of writing assessment and social justice. Specifically, in engaging with the push-pull legacy toward language use and race that is found at HBCUs, the author indicates ways we might enable teachers, administrators, and students to resist monolingual, racialized consequences embedded in their views of writing assessment and rethink the foundational measurement concepts of reliability, validity, and fairness.