This article presents the partial research findings on financial instability as a risk factor for the recurrence of homelessness among families enrolled in a Housing First project in the City of Brno (Czech Republic). The project represents an evidence-based social innovation focused on ending families’ homelessness. The research was designed as a Randomised Controlled Trial study accompanied by a qualitative evaluation. The data were collected through questionnaires, individual interviews, and focus groups. In the results section we follow the logic of a financial stability model and conclude that research results on financial stability overall did not prove to be statistically significant on a short-term scale. In the discussion, we state that prolonged material poverty combined with the nature of the Czech housing benefit system and the experience of residential alienation could increase the risk of the recurrence of homelessness for families. A crisis financial fund was established in an effort to prevent this.