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Although gentrification creates the opportunity to lessen segregation at urban public schools, it simultaneously generates an array of challenges for school leaders. This study asks how school leaders at a public school in New York City are conceptualizing and responding to the problems posed by gentrification-influenced integration. Drawing on qualitative data from interviews with school leaders and quantitative data from the Decennial Census and the American Community Survey, this study finds evidence that bridging the gap from desegregation into true integration, facilitation of social mixing across races and classes, and pressures from privileged parents seeking to further the cycle of advantage for their children are some of the greatest challenges present at gentrifying public schools. Research and policy implications are discussed.