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This paper explores two previously unexamined court challenges brought by Black settlers in the territorial period of Oklahoma (1889-1907). In Oklahoma, courts heard more challenges to segregated schools than in any state as Black pioneers fought legislation that segregated previously integrated schools. In the territory, Black families sought the protection of the courts whose judges were federal appointees. During this pivotal time in the determination of citizenship rights for Blacks, this paper asks: how did Black families perceive their rights to education and the role education would play in their ability to access full citizenship status? How would educational access be used by whites to deny citizenship rights to Blacks? Oklahoma’s Territorial courts tackled these questions.