A prominent demographic trend throughout the industrialized world is population aging. Concerns about economic growth and labour force shortages have led many European nations to enact policies aimed at prolonging working life. Understanding how paid work among late-middle-aged and senior adults is associated with health is therefore important. Using a sample of persons who were 50–75 years of age in 2015 from waves six (2015) and seven (2017) of the Survey of Health, Ageing and Retirement in Europe (n = 38,884), this study shows how a comprehensive set of six workforce involvement/transitions patterns are associated with health. The results show benefits of paid work, especially among respondents having financial difficulties. There is further heterogeneity by gender. The more fragmented employment histories of 50–75-year-old women are associated with stable paid work being of less benefit for addressing financial difficulties and with their health being especially vulnerable to unemployment while they are undergoing financial troubles.