Among aging employees, sleep problems are prevalent, but they may have serious consequences that are poorly understood. This study examined whether sleep problems are associated with subsequent disability retirement. Baseline questionnaire survey data collected in 2000-2002 among employees of the city of Helsinki, Finland, were linked with register data on disability retirement diagnoses by the end of 2008 (n = 457) for those with written consent for such linkages (74%; N = 5,986). Sleep problems were measured by the Jenkins Sleep Questionnaire. Cox regression analysis was used to calculate hazard ratios and 95% confidence intervals for disability retirement. Gender- and age-adjusted frequent sleep problems predicted disability retirement due to all causes (hazard ratio (HR) = 3.22, 95% confidence interval (CI): 2.26, 4.60), mental disorders (HR = 9.06, 95% CI: 3.27, 25.10), and musculoskeletal disorders (HR = 3.27, 95% CI: 1.91, 5.61). Adjustments for confounders, that is, baseline sociodemographic factors, work arrangements, psychosocial working conditions, and sleep duration, had negligible effects on these associations, whereas baseline physical working conditions and health attenuated the associations. Health behaviors and obesity did not mediate the examined associations. In conclusion, sleep problems are associated with subsequent disability retirement. To prevent early exit from work, sleep problems among aging employees need to be addressed.