The aim of this thesis is to examine whether social enterprise provides employment and enterprise opportunities for homeless people. The homelessness literature has paid little attention to this changing policy landscape. This thesis seeks to contribute to the academic literature on homelessness and social enterprise and explores the ways in which social enterprise meets the employment and enterprise needs of homeless people. The research for this thesis focused on homelessness social enterprises based in England. The approach was guided by the critical realist method and included the construction of a database, multiple case study organisations, and interviews with homeless people and social enterprise leaders. An observational element was also incorporated in the case study organisations and wider social enterprises operating in the homelessness field. The research found that labour market exclusion of homeless people usually occurs early on in the lifecycle and was embedded over time through individual, inter-personal and structural elements. As a response to this social problem the research uncovered a number of existing and emerging homelessness social enterprise models. Organisations adopting these approaches occupy different sectors of the economy and provide a wide variety of (predominately service sector) jobs. The evidence also suggests they adopt different legal forms and use hybrid funding sources. Moreover, they cluster into particular types and most are not currently able to operate without the support of a host organisation. Instances of homelessness social enterprises were found to be increasing but clear challenges concerning their development came from exogenous economic and political factors. These developmental challenges were found to be buffered against by social elements endogenous to social enterprises. Also various advantages and disadvantages were related to each model, which critically highlighted that some approaches were better suited than others to assist homeless people into employment and enterprise, especially those experiencing ‘deep exclusion’ issues