The Wales (Housing) Act 2015 introduced a preventative approach to addressing homelessness which 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 pris...