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Background As the workforce ages, older employees face increasing challenges in adapting to evolving job demands, including technological changes and persistent occupational risk factors such as shift work and physically demanding tasks. Workability is a reliable indicator of older workers’ capacity to meet both physical and psychological demands. ProAgeing study is a multicentric study focused on workers older the 50 years. In this work we explore longitudinal workability, health, work-related, and psychosocial factors, as well as their interplay, in a population of older workers.Methods Participants completed self-reported questionnaires at baseline and after one year, including the Work Ability Index (WAI), technostress, sleep quality, perceived stress and health, and psychosocial risk factors. Multiple linear regression was used to assess predictors of changes in WAI. Subgroup analyses explored differences across occupational roles (bank employees, administrative employees, and manual workers).Results Of the 470 workers enrolled, 356 (76%) completed the follow-up. A significant decrease in average WAI score was observed over 12 months (-1.2 points, p<0.001), mainly in subscales related to work demands and physical illness. Technostress levels slightly decreased, suggesting adaptation over time. Bank employees showed less favorable trends than manual workers, suggesting that digitalization and higher job demands significantly affected employees’ well-being, particularly older workers. Improvement in perceived health and reduced stress mostly contributed to enhance workability.Conclusion These findings suggest the need for targeted interventions to improve health and reduce stress for ageing workers in order to support their well-being and consequently their workability.