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Homelessness has been a problem in New York City (NYC) for decades. Part of the problem is children who grew up in the shelter system and then returned as adults, a phenomenon known as 2nd-generation homelessness. Literature indicates that no researchers have interviewed second-generation homeless adults about their experiences. The purpose of this study was to explore the experience of 2nd-generation homelessness from the perspective of homeless adults returning to the shelter system. The sample included 1 second-generation homeless adult and 10 case managers at Tier II homeless shelters. Interviews were conducted and data were analyzed using hand coding to uncover themes amongst the interviews. The themes found were: lack of information and resources, generational homelessness is passed down, people should learn from their parents' mistakes, comfort in the homeless shelter system, money, parental abuse and neglect, the role of the case manager, taking advantage of the shelter system, and mental health. The other topics that were discussed on multiple occasions but did not fit into larger categories are: education, drugs and alcohol, lack of family assistance, and activities of daily living. Findings from this study inform social change by indicating a clear need for input from homeless families and case managers when developing interventions to address second-generation homelessness. Future policymakers should include staff and clients when developing ways to address homelessness in New York City. The views and opinions expressed in this manuscript reflect the personal views of the researcher and interviewees; they do not represent the views of NYC Department of Homeless Services or its providers.