In this paper we explore the responses of a group of long-term unemployed men to chronic labour market insecurity and ‘active’ labour market policies promoting individual responsibility for employability. We draw from an evaluation of a recent pilot scheme: the UK Employment Retention and Advancement Demonstration. We identify a range of responses, shaped through experiences which reflect gender, class, and age divisions. Despite significant labour market disadvantage, some of the men responded by proactively engaging with the employability agenda. Drawing on qualitative longitudinal data, we follow the trajectories of the men in work, examining how they fared in insecure, precarious labour markets. We conclude by looking at the strengths and limitations of the current policy agenda, suggesting that more creative ways need to be found to engage some of the most disadvantaged in the reskilling agenda and that employers are currently a ‘weak link’ in the package of support provided.