The purpose of the present study was to explore the lived experiences and psychological dynamics of current and formerly homeless adults on the island of Oahu, ages 18 to 55 years old. There are four key findings in this study. First, analysis of the data revealed some key psychological dynamics: addiction issues, mental health issues, childhood trauma, and fear (including the absence of trust). In addition, the factors that led most of these people to the streets were multi-faceted. For most of the participants, it was not one event but rather, a series of progressive difficulties that seemed to cascade into multiple areas of their life. Numerous individuals reported having a genuine fear and mistrust of engaging with services and providers. It was evident from the findings that the most influential assistance in moving off the streets came from family. The present study assists service providers in their understanding of this often-misunderstood population. The findings of the study are contextualized to residents living in Hawaii and may not be transferable to homeless individuals in other states.