The transition from employment to retirement is changing dramatically in Canada and other industrialized societies, with a decreasing proportion of working life being spent in stable career progression. This study used a sample of 2,592 subjects, aged 45 to 64, from the 1994 General Social Survey of Canada (GSS): Cycle 9, to describe situations of later-life career disruption (LLCD) in older workers in Canada and to investigate the association between LLCD and self-rated health. Results showed that a large proportion of older Canadian workers had experienced such LLCD as job interruption and job loss. Experience of job loss and job interruption over the prior 5-year period was found to be significantly associated with poor self-rated health, after controlling for age, education, body mass index, and activity limitation. However, after excluding respondents whose LLCD was known to be due to poor health, job interruption and job loss were separately found not to be significantly associated with poor health. The complexity of the findings and the direction of causation between LLCD and self-rated health, as well as some methodology issues, are discussed. Areas of future research are indicated.