Housing First (HF) aims to overcome homelessness by offering immediate, independent accommodation in the community. In doing so, the model seeks to provide a foundation for client centred support that enables recovery from the ‘multiple and complex’ needs that multiply excluded homeless (MEH) adults experience. The majority of HF literature has focussed on the model’s very positive housing related outcomes. However, outcomes related to recovery and desistance have been less clear. This article draws on a qualitative, longitudinal evaluation of a HF service in a northern English city, following 18 MEH adults over 16 months in their HF tenancy. A situational approach was used to explore participants’ ability to utilize the foundation provided by HF achieve outcomes related to recovery and desistance. Findings demonstrated the importance of participants’ biographies in determining their ability to progress towards these outcomes. A key output of the article is a typology of participant’s biographies that was predictive of their trajectories in HF.