When looking at clients with a long history of unemployment and substantial health and/or social problems, stories of success (in terms of moving from being on cash benefits to getting a job) are limited. Thus, when a client does manage to gain employment or enter education, it represents an unusual1 story of success seen from a political, organisational and individual perspective. In this article, we investigate empirically what can be learnt about current active labour market policies from these client cases. Methodologically this is explored through interviews with former clients who have managed to find a job despite dealing with complex health or social issues, and interviews with their former caseworkers. Thus, the article aims to provide insights into the crucial elements in making the move from vulnerable unemployed to being ready for a job, as well as finding it and keeping it.