This dissertation explores previously unstudied and undiscovered court challenges brought by Black settlers during Oklahoma’s territorial period (1889-1907) in the United States. These Black pioneers challenged new legislation that segregated previously integrated territorial schools. Black citizens in Oklahoma Territory had equal rights to land under the Homestead Act and the territory’s Organic Act. They had historic access to integrated education in other states, in Indian Territory, and on military posts. Yet in the legal era that increasingly determined that segregation was equality after the Plessy v. Ferguson decision in 1896, Black settlers began to see the narrowing of their rights. These families sought the protective wing of the nascent courts whose judges were federal appointees. Territorial courts heard more challenges to segregating schools than in any state. This was a time of unique confluence of law, public education, and defining Black citizenship. Would schools be the gateway to full civic and economic participation? Or would schools be a gatekeeper, denying access to some in order to maintain dominance for others? Territorial courts tackled these questions. Historians frequently have argued that the country’s failure to provide Blacks with civil rights resulted from its failure to redistribute land and/or from a premature end to federal oversight in the South after 1876. But in Oklahoma Territory, neither of these variables was in play: Black settlers had land, federal oversight, and the ability to vote. Nevertheless, they watched their civil rights diminish as the popular will established segregated education. The loss of access to education was key in re- inscription of second-class citizenship for Black Americans.