The Wales (Housing) Act 2015 introduced a preventative approach to addressing homelessness that impacted on prison leavers in Wales. Since the same changes will take effect in England from October 2018, this paper provides early insight into how new preventative duties have been implemented in Wales. Drawing on interviews with 114 stakeholders and 75 prison leavers, we report that the promise associated with a preventative agenda is presently not fully realised. We contend that resettlement activity might be improved if it was better incentivised and facilitated inside the prison wall. However, we also suggest the time has come for more radical options to be pursued to address homelessness amongst prison leavers. We argue against short prison sentences, which are so often causative of homelessness, and for providers of probation services to be better incentivised and resourced to take a more active role in meeting accommodation needs.