Objective: This article examines the relationship between aging and drinking problems among mature workers and the moderating effects of positive alcohol expectancies (PAEs) and workforce disengagement. Method: This longitudinal study collected data on mature adults (i.e., retirement eligible) in three employment sectors (i.e., construction, manufacturing, and transportation) over five periods: T1 was 6 months before their retirement eligibility date and T5 was 4 years afterward. AtT1, 1,122 subjects participated in the survey; at T5, 917 participated in the survey. Problem drinking was assessed in all five waves by the Drinking Problems Index. PAEs were measured at T4 and T5 by the Alcohol Outcomes Expectancies Scale. Workforce disengagement was assessed by subjects' employment status at T5 (i.e., still working despite eligibility versus fully retired/not working). Control variables were employment sector, age at T1, and gender. Results: PAEs moderated the relationship between aging and drinking problems: High PAEs were associated with an increase in drinking problems, whereas low PAEs were associated with a decrease in drinking problems. With regard to disengagement, continuing to work amplified the moderating effects of PAEs on the relationship between aging and drinking problems, whereas the moderating effects of PAEs were attenuated for the fully retired. Conclusions: This study provides further evidence of the significance of PAEs and drinking problems among mature adults, particularly as they are conditioned by disengagement from work. Implications for employee/member assistance program are discussed.