This study examines gender differences in postretirement employment, using the first eight waves of Health and Retirement Study data. Gender is shown to be an important factor in understanding transitions into postretirement employment. Forty-seven percent of retirees ( n = 3,590) experienced postretirement employment, with 43% of retired women making the transition, compared with 50% of retired men. Marital status, earnings, and household wealth were significant only when gender interaction terms were introduced due to countervailing effects by gender. For women, being married and having high household wealth were negatively associated, and higher earnings positively associated, with labor force reentry; for men, wealth and earnings had the opposite effect. Hazard models show that divorced and separated women have a greater likelihood of labor force reentry than married women and that this difference increases with time out of the labor force, suggesting push factors that derive from economic vulnerability.