Those aged over 50 experience the longest spells of unemployment and have particularly poor outcomes on government funded welfare-to-work programmes. Recent policy shifts in the UK have brought an end to differentiated labour market programmes for older social security claimants, but at the same time have extended and intensified the principle of welfare conditionality as part of UK active labour market policy. Using analysis of new data from 44 qualitative interviews with benefit recipients aged 50+ this paper explores older unemployed people’s experiences of the UK’s increasingly conditional welfare system. It concludes that a lack of personalisation results in an ineffective employment support system that neither recognises the skills and attributes of an ageing workforce nor provides appropriate support to help older people to overcome the barriers that routinely inhibit their labour market participation