Objective: This study compared changes in criminal justice contact, quality of life, and social connectedness over a 12-month follow-up period between participants in two Housing First configurations (scattered site [SS] and congregate site [CS]). Methods: A longitudinal, quantitative design was utilized for this ecological study. Changes in individual outcomes over time were compared for SS and CS participants who completed both baseline and 12-month follow-up surveys (N=63). Results: The number of contacts with various types of criminal justice system channels differed significantly between SS and CS participants, decreasing significantly among SS participants and increasing significantly among CS participants. The two groups did not differ on quality-of-life outcomes or social-connectedness measures, with the exception of case management engagement, whereby a greater proportion of SS participants disengaged from this service over time compared with CS participants. At follow-up, significant within-group changes over time emerged, with increased boredom reported among SS participants, whereas CS participants reported improvements in social relationships, with fewer reporting losing their temper. Conclusions: The findings supported the notion that the Housing First approach has the potential to significantly improve the lives of persons who have experienced chronic homelessness, a traditionally marginalized and vulnerable group. Over time, this may result in a reduction in the use of acute services, thereby reducing societal costs. The challenge remains to identify the suitability of particular configurations of housing and support and how service delivery can optimize individual outcomes so positive outcomes are maintained in the longer term.