Age-related changes in cognitive abilities are well-documented, and a very important indicator of health, functioning, and decline in later life. However, less is known about the course of cognitive functioning before and after retirement and specifically whether job characteristics during one's time of employment (i.e., higher vs. lower levels of mental work demands) moderate how cognition changes both before and after the transition to retirement. We used data from n = 4,182 (50% women) individuals in the Health and Retirement Study, a nationally representative panel study in the United States, across an 18 year time span (1992-2010). Data were linked to the O*NET occupation codes to gather information about mental job demands to examine whether job characteristics during one's time of employment moderates level and rate of change in cognitive functioning (episodic memory and mental status) both before and after retirement. Results indicated that working in an occupation characterized by higher levels of mental demands was associated with higher levels of cognitive functioning before retirement, and a slower rate of cognitive decline after retirement. We controlled for a number of important covariates, including socioeconomic (education and income), demographic, and health variables. Our discussion focuses on pathways through which job characteristics may be associated with the course of cognitive functioning in relation to the important transition of retirement. Implications for job design as well as retirement are offered.