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Returning to employment after a period on welfare benefits is particularly challenging for people aged over-50 and those with health conditions. We explore the unemployment-to-employment transitions made by clients engaging with the Work Programme (WP); the UK Government’s main return to work (RTW) initiative. It supports two main groups of welfare benefit claimants - JSA, for people who are unemployed but capable of work; ESA, for people with a disability that makes it more difficult to work.The data were from the SOPIE cohort (13 461 unemployed clients aged 18–64, who entered the WP in Scotland between April 2013 and July 2014). For clients who started a job, unemployment and employment spells during their two-year period in the WP were determined and sequence index plots produced using Stata version 14. These visualisations were explored by age and benefit type.Job start rates were: ‘JSA clients under-50’, 65%; ‘JSA clients over-50’, 49%; ‘ESA clients under-50’, 23%; ‘ESA clients over-50’, 14%. Despite the lower numbers of ESA clients with a job start the visualisations revealed that these clients (both under and over-50) were as likely to sustain employment as JSA clients. Analyses also investigated employment by Standard Occupational Classification and full versus part-time.Visualising longitudinal employment data provides new insight into the relationship between age, health and the RTW process. Although people receiving health-related benefits (ESA) enter employment at lower rates, they can sustain employment similarly to JSA clients, suggesting support for policies aiming to reduce the disability employment gap.