The growing interest in the impact of lifetime occupational exposures on later-life health underscores the need to expand and evaluate the quality of data resources. The present study took advantage of a retrospective life history survey fielded within the context of the Health and Retirement Study to assess the accuracy of retrospectively obtained information on job history. We evaluated hypotheses related to job history and respondent characteristics to understand more about factors associated with recall accuracy. We used data from the Life History Mail Survey (LHMS), a self-administered survey conducted in 2015 and 2017. We compared the match rate of work status collected in the LHMS questionnaire with data collected concurrently during HRS core face-to-face or phone interviews from 1992 through 2016 with respect to jobs held at the time of the interview. We also conducted a limited set of comparisons of occupation and industry match. The sample was 61.79% women, 82.12% White, and 8.57% Hispanic with a mean age of 74.70 years. The overall work status match rate was 83%. Jobs held longer ago were recalled with less accuracy. Jobs held for longer durations and that were full-time rather than part-time were recalled with greater accuracy. More complex job histories that involved a larger number of jobs were also associated with a lower match rate. Higher levels of conscientiousness and cognitive functioning were both associated with a higher match between the two sources of work status information. The occupation match rate was 69%, and the industry match rate was 77%. A self-administered, paper-and-pencil questionnaire attempting to measure decades-long histories of autobiographically important dimensions of life can provide reasonably accurate historical employment information. Several factors are likely to influence the relative accuracy of recalled information.