Employment re-entry opportunities decrease with age. For middle-aged welfare benefit recipients, employment obstacles connected to age exacerbate further disadvantages connected to welfare receipt. At the same time, there is considerable diversity in middle-aged welfare benefit recipients’ long-term employment trajectories, which has thus far received little attention. Policies aim to increase labour market participation at higher ages. To this end, it is important to understand specific difficulties and to be realistic when formulating goals for people with very diverse types of employment histories. Using large-scale register data, this paper’s focus is on a cohort aged 45–54 in August 2012 in Germany. Sequence analysis aids in identifying characteristics relevant to employment histories over the past 19 years, from January 1993 to July 2012. Subsequent employment outcomes over the time span September 2012 to December 2018 are investigated, differentiating between jobs of different quality, and effects of training programmes on these outcomes are analysed using entropy balancing methods. Findings are that middle-aged welfare recipients’ employment biographies are very diverse, ranging from very little employment experience, over long histories of intermittent employment, to long continuous employment histories. Employment history attributes significantly affect employment prospects. The analyses further show that it is not too late to invest in skills, independent of employment history type.