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Retirement timing can have important health implications. Little is known, however, about older adults’ views on this issue and whether they consider it better to retire later, earlier, on time or anytime. This knowledge gap about older adults’ views is particularly true outside North America and Europe. This qualitative study aims to examine older Chileans’ ideas about the relationship between retirement timing and health and to explore gender and class patterns in qualitative themes identified, knowledge which may strengthen quantitative population-based approaches. Framework analysis was conducted on qualitative accounts from a purposive, non-random sample of 40 older Chileans in six focus groups, stratified by gender and class as marked by lifetime occupation. Transcriptions were coded by two independent reviewers (inter-coder reliability = 81%) according to four deductive categories of retirement timing as well as inductive coding of emergent themes. The content and sequence of codes were visually represented in MAXQDA’s document portraits and illustrated with descriptive quotes. Results indicate that participants’ views about when to retire in order to maximise health did not highlight retirement age or timing (later, earlier, on time, anytime). Instead, these older Chileans emphasised that the optimal retirement age depends on other conditions, such as employment quality, retirement income and gender. These views were patterned: lower occupational-class participants emphasised income and job hazards, higher-class males emphasised job satisfaction and higher-class females emphasised gendered patterns. Women and lower-class participants were relatively more favourable to earlier retirements than men and higher-class participants. Overall, qualitative analyses of lay perspectives from understudied country contexts complement and extend population-based models focused on timing or retirement age, suggest specific characteristics of retirement transitions that may moderate health consequences, and highlight class and gender differences in views of retirement timing. More research is needed using mixed-methods approaches and leveraging both purposive and random samples.