As the proportion of older adults in the United States grows, there are significant concerns surrounding economic well-being in retirement. The two major components of the U.S retirement income system, Social Security and employer-sponsored retirement plans, have undergone significant changes that erode financial security in retirement. Working longer has been proposed to help older adults overcome deficits in retirement income. However, even when motivated to work, many older adults face significant challenges in the labor market, particularly those who are unemployed or displaced. In the current study, secondary data from the Health and Retirement Study (HRS) is used to identify demographic and contextual factors associated with unemployment, displacement, and reemployment (among those who are displaced at Time 2) among older adults. Logistic regression is used to examine the influence of race/ethnicity, gender, education, relationship status, health status, income status, geographical location, eligibility for retirement/age, and sector of employment on unemployment, displacement, and reemployment. Results suggest being of an “other” race, being married, being in fair to poor health, and having household income below the poverty threshold increased the odds of employed while being previously employed in the service sector reduced the odds of unemployment. All else equal, being African American and living in the West increases the likelihood of displacement among older adults while being female, living in poverty, and being eligible for retirement (aged 62 and older) reduces an older adult’s chances of being displaced. Finally, all else equal, being African American, living in the Northeast, and being eligible for retirement (aged 62 and older) reduced the likelihood reemployment at Time 2. The major implications of these findings for research, policy, and practice are discussed.