Objectives: Current demographic trends, such as society aging, the spreading of chronic diseases, as well as early retirement choices, lead to the dwindling labor market population. Taking into consideration the foregoing tendencies and their consequences, the issue of the shrinking labor force resources seems to be the most important challenge for the labor market. In response to it, this paper identifies individual and institutional causes of withdrawal from the labor market, and explores the views of Polish stakeholders on existing strategies for the occupational re-integration of persons with chronic diseases (PwCDs). Material and Methods: Polish results of 2 European projects: “Participation to Healthy Workplaces and Inclusive Strategies in the Work Sector” (the PATHWAYS project) and “The Collaborative Research on Aging in Europe” (COURAGE in Europe) complemented each other. The cross-sectional population data and data from stakeholders’ interviews were used. Results: The authors identified several causes which could encourage people to withdraw from the labor market before attaining the official retirement age at 3 different levels: individual, occupational, and institutional. Although research has shown that the macro-level situation is crucial to staying occupationally active, in Poland stakeholders have reported the lack of effective coordination in the implementation of policies for the occupational re-integration of PwCDs. Conclusions: A decision to cease work prematurely reflects a combination of many different factors, such as individual determinates, work characteristics, personal convictions, and systemic solutions. The study demonstrated that, despite the awareness of the dwindling resources of labor force, the employment-related challenges faced by PwCDs as well as people who are close to the retirement age remain unaddressed. Int J Occup Med Environ Health. 2019;32(5):695–721