This article draws upon findings from the New York Services Study, a Federally-funded qualitative study conducted in practice settings representing two fundamentally different approaches to serving homeless adults with serious mental illness and co-occurring substance abuse. The findings yielded four themes—cumulative adversity, individual acts of kindness in a system designed to control, discordant case managers’ perspectives, and the benefits of permanent housing. Recommendations for practice include respecting individuality, being sensitive to previous traumas, and working to achieve housing security sooner rather than later. Future research is needed to study the micro-level contexts of service delivery and how they inhibit or encourage engagement in care.