This article presents findings from a qualitative study of 14 individuals residing in extended-stay hotels after housing displacement. Framed in ecosystems and structuration theory, the purpose of this study was to understand social service barriers experienced by help-seeking residents. Participants were engaged in in-depth interviews and asked about challenges faced when they reached out for assistance to prepare for stable housing. Reported barriers included negative interactions with social service personnel, cumbersome agency processes, and insufficient/inappropriate resources. Hotel residents identified guidance, compassion, and advocacy as interventions practitioners can use to support client transitions to stable housing.