Gulino v. Board of Education is a class action employment discrimination lawsuit awarding approximately $1.8 billion to over 5,200 Black and Latine teachers in New York City in response to a racially discriminatory teacher licensure exam. This essay explores Gulino as an attempt at assessment reparation. Using frameworks of harm and constructive-based repair, the essay examines the harm-based logic of the ruling that provides restitution for individual teachers but does not reduce the broader discriminatory pattern of licensure systems. We then explore how a constructive approach to repair might have worked, and might still work, through participatory policy analysis, community answerability, and antiracist assessment. We apply insights from Gulino to current policy shifts loosening teacher licensure requirements and potential lawsuits against edTPA.