This chapter uses archival research, contemporary reporting, and oral history interviews to explore developments in fair and affordable housing in Westchester County, New York from 1983 to 1992. Though Westchester was largely liberal politically, many of its municipalities resisted housing solutions that raised the specter of greater racial and class heterogeneity and sought to thwart accommodations designed to serve the increasing ranks of the county’s homeless population. At the same time, I argue that new housing advocacy groups, religious and secular, emerged as major players who negotiated with layers of government and local opposition to achieve gradual, though still insufficient, “traction” for affordable housing and transitional housing for the unsheltered. In doing so, they fought against the “friction” of what scholars have called the “aestheticization of exclusion” through restrictive zoning, conservative ascendancy in national politics, and often formidable local groups who opposed affordable housing. The progress made on affordable housing and transitional accommodations for the homeless was made without explicitly confronting the issues of fair housing and residential segregation, which continued to fester into the 2000s.