Insecure housing—particularly for low-income groups—constitutes a critical and enduring social problem. While Permanent Supportive Housing (PSH) initiatives show promise as a solution to mitigate this issue, research assessing their impact remains limited. This paper makes three contributions to the empirical PSH literature: it develops a novel framework to measure the success of PSH tenancy outcomes; it expands the evidence-base to consider the role of tenancy issues and provider-initiated tenancy-sustainment supports; and it provides new evidence on a single-site PSH initiative in Queensland (Australia)—Brisbane Common Ground (BCG). We use 10 years’ worth of administrative data on all 417 tenancies—both concluded and ongoing—taking place since the onset of BCG in July 2012 and up to November 2022. Our main analyses combine descriptive statistics, event-history analyses, and logistic regression models. Results reveal significant heterogeneity in the probability of experiencing positive PSH tenancies across socio-demographic groups, the intervening role of tenancy issues, and the partially protective role of provider tenancy-sustainment initiatives. The results, however, vary depending on the lens through which PSH tenancy outcomes are viewed. These findings stress the need for targeted PSH strategies that better cater for the complex needs of specific subgroups of tenants.