This study reconfirmed recent findings, that being “housed” does not automatically result in an individual no longer being “homeless”. Recognizing that homelessness is, in large part, a psychological state of disconnection from family, friends, social networks, and communities, rather than simply a state of not having a roof over one’s head. A more holistic view of these disconnections leads to the conclusion that more work needs to be undertaken to assist homeless individuals in re-developing strong formal and informal social support networks. Failure to develop such networks will inevitably lead to individuals re-entering the cycle of homelessness. Supports such as recreation, mental and physical health, skills development training/social enterprise, and community building programs will assist individuals in making the psychological transition from homelessness to safety that is required to ensure sustainable housing works.