Objectives: Five-factor model (FFM) personality traits, including higher conscientiousness and lower neuroticism, are associated with lower risk of dementia and cognitive impairment. In this research, we test whether retirement status moderates and/or mediates the relation between personality and cognitive impairment. Method: We used data from the Health and Retirement Study (N = 9899), a longitudinal study of Americans over the age of 50 years, to examine moderating and mediating associations between personality traits and retirement status on risk of dementia and cognitive impairment not dementia (CIND) over an 8-10 year follow-up. Results: Personality and retirement each had strong, independent associations with risk of dementia and CIND. There were not, however, strong or consistent, moderating or mediating associations between personality and retirement predicting impairment risk. Discussion: Overall, these results indicate that personality and retirement are independent risk factors for incident cognitive impairment. Mechanisms other than retirement are likely to explain this association.