By investigating the history of Black maroons in their journey from Florida to Indian Territory, this chapter traces the expansion and reconfiguration of marronage practices within and beyond the Gulf South. Specifically, Paul Barba is concerned with how Black fugitives leveraged their Florida experiences to reforge viable communities in Indian Territory, making marronage widespread, coordinated, and even militarized in the borderlands post-Indian Removal. Thus, in the 1840s and 1850s, Black maroons became, yet again, a real threat to U.S. (and Indigenous) claims to power, despite their seeming capitulation to U.S. federal authorities in the Florida theater during the Second Seminole War. For the Black rebels, the fight for freedom and autonomy had no geographical bounds.