Despite a legally-mandated right to shelter and extensive outreach efforts, an estimated 3,675 homeless individuals were living on the streets of New York City in 2018. Through interviews with 43 unsheltered homeless individuals in the borough of Manhattan (age range 21–74 years), this qualitative study examined barriers they face in accessing housing and other services as well as experiences surviving on the street. Through thematic analysis of the interview data, the most common barriers found were obtaining required identification documents, lack of accessibility of shelters amid complex healthcare needs, waiting as part of the process, and exclusion of pets from shelters and housing options. Themes capturing survival on the street included sleeping safe, avoiding shelters, and meeting daily needs. Virtually all barriers street homeless New Yorkers face stem from bureaucratic policies that, however well-intentioned, do not address their diverse needs. Thus, long delays and poor communication, combined with crowded, unsafe shelters, lead to frustration and alienation. While homelessness is ultimately the result of a severe and chronic shortage of affordable housing, creating accessible, safe, pet-friendly shelter and safe haven options and instituting a smoother, more transparent process for moving from the streets could substantially reduce street homelessness.