This paper is an exploration of a dilemma that is central to the place of day centres in tackling single homelessness and raises issues for social work more generally. On the one hand, day centres provide vital services to a vulnerable group in a safe, non-threatening and non-judgemental setting; on the other hand, in doing so, they are believed to impede opportunities for personal change. The paper draws on findings from a research study which compared and contrasted the priorities of single homeless people with multiple support needs with the priorities of support services, exploring the role of encounters between service users and agencies in either overcoming or reinforcing multiple exclusion homelessness. This paper focuses on evidence about the use of day centres. It seeks to draw on theological insights to explore day centres as ‘places of sanctuary’ whose largely unconditional accessibility enables them to serve as both a last refuge for the victims of multiple rejection and a safe place to confront the past. This paper will take the debate about conditionality in welfare provision beyond the field of homelessness to address one of the oldest dilemmas of social work: how to facilitate change while respecting people's free agency.