We sought to characterize the association between a forensic event (arrest or incarceration) with housing vulnerability and mental and physical health status over a four-year follow-up among a cohort of homeless and vulnerably housed individuals in Vancouver, Toronto and Ottawa. Data were obtained from the Health and Housing in Transition Study, a prospective cohort study of homeless and vulnerably housed individuals between 2009 and 2012. Participants were interviewed in-person at baseline (N = 1190) and at four annual follow-up time points. We used generalized estimating equations to characterize the independent associations between a forensic event and the number of residential moves and SF-12 physical and mental health component scores over the four-year follow-up period. We analyzed data from 1173 homeless and vulnerably housed participants. Forensic events were reported by 446 participants at baseline. In multivariate analyses, a history of forensic event in the preceding twelve months was independently associated with an increased number of residential moves over the four-year follow-up period (ARR 1.24; 95% CI 1.19–1.3). It was not, however, independently associated with a change in physical or mental health status (respective ß-estimates; 95% CI: -0.34; -1.02, 0.34, and -0.69; -1.5, 0.2). Female gender and a history of problematic substance use were significantly associated with all three primary outcomes. This suggests arrest or incarceration is associated with increased housing vulnerability. The results underline the importance of supporting individuals experiencing arrest or incarceration with post-release planning in order to obtain stable housing after discharge.