In exchange for their receipt of conditional benefits such as JobSeekers Allowance and Universal Credit, people experiencing homelessness are expected to engage in mandatory job search or other work-related activities. However, many homeless people have become alienated from mainstream employment support as a result of difficulties in meeting these compulsory conditions. Recognising their exclusion from the mainstream welfare system, this chapter focuses on an alternative source of employment support for homeless adults - that offered by third sector homelessness organisations. Drawing on new data from interviews with homelessness practitioners, it uncovers a range of employment-related support available to homeless people accessing support from third sector providers. It then considers two key potentially contradictory issues. First, whilst a range of employment-related support services delivered by third sector organisations’ own programmes and initiatives are identified, much of this appears to be focussed on mitigating the impacts of the increasingly conditional nature of the statutory welfare system. Second, while appearing critical of the increasingly conditional statutory system and the impacts that a punitive welfare state is having on those they are supporting, some of the approaches adopted by these agencies also incorporate elements of conditionality.