Like many West Indians, mixed-race Jamaican immigrants enter the United States with fluid notions about race and racial identifications that reflect socio-political events in their home country and that conflict with the more rigid constructions of race they encounter in the U.S. This dissertation explores the experiences of racially mixed Jamaicans in South Florida and the impact of those experiences on their racial self-characterizations through the boundary-work theoretical framework. Specifically, the study examines the impact of participants’ exposure to the one-drop rule in the U.S., by which racial identification has been historically determined by the existence or non-existence of black forebears. Employing qualitative data collected through both focus group and face-to-face semi-structured interviews, the study analyzes mixed-race Jamaicans’ encounters in the U.S. with racial boundaries, and the boundary-work that reinforces them, as well their response to these encounters. Through their stories, the dissertation examines participants’ efforts to navigate racial boundaries through choices of various racial identifications. Further, it discusses the ways in which structural forces and individual agency have interacted in the formation of these identifications. The study finds that in spite of participants’ expressed preference for non-racialism, and despite their objections to rigid racial categories, in seeking to carve out alternative identities, they are participating in the boundary-making of which they are so critical.