Objectives: This study aims to (i) document the changing proportions of older persons with health insurance in a period of policy change, (ii) examine why older persons do and do not purchase health insurance, and (iii) discuss these findings in relation to implications for current and future cohorts of the aged. Method: Data from the Private Health Insurance Administrative Council and the ABS are used to estimate cross-sectional and cohort shifts in health insurance coverage among persons aged 55 years and over. Results: Prior to recent reforms, approximately 37% of persons aged 55 years and older have hospital health insurance compared with 45% in 2001, with considerable variation in coverage by age and sex. Conclusion: Health insurance coverage has increased among older Australians, albeit disproportionately. Affordability remains a key issue for older Australians and may become more problematic in future age cohorts.