As US schools return to the levels of segregation that existed when many initial desegregation orders were established and concentrations of poverty are escalating, the judicial tools in place to achieve integrated schools have shifted. In its most recent ruling on school desegregation, "Parents Involved in Community Schools v. Seattle School District No. 1", the US Supreme Court required school districts to implement less race-conscious student assignment plans when attempting to achieve racial diversity throughout their schools. In this article, I explore the nexus between current race-neutral judicial preferences, racial integration, and the segregated realities that are present across many US school districts. Specifically, I examine the challenges of one urban school district, Omaha Public Schools, who utilizes a race-neutral student assignment policy in its integration efforts. I pay particular attention to the history around racialization in the Omaha metropolitan area and how it impacts the district's efforts to achieve racial diversity in its schools. Finally, I conclude with a discussion on potential challenges urban school districts may face in trying to achieve their intended diversity goals if new methods of student assignment are not considered in shifting sociopolitical contexts.