Housing First (HF) provides independent accommodation in the community to Multiply Excluded Homeless (MEH) adults. The principle of “choice and control” is central to the model and has been positioned as an effective mechanism for enabling MEH adults to guide their recovery or desistance. However, the theoretical literature on decision-making emphasizes that individual choices are influenced by a complex range of factors. This article describes how Situational Action Theory (SAT) can be adapted to guide a detailed qualitative analysis of how MEH adults make choices. It is argued that the SAT can support a better understanding of the complex personal and environmental factors that influence individual choices during journeys of recovery and desistance. The article presents two vignettes using data from a longitudinal study of an HF service to show how SAT was used to make sense of key choices made by MEH adults.