Data from the 2011 Survey of Older Persons in Thailand examines the association between preparations for old age (financial, health, caregiving, living arrangements, and spiritual) and three measures of well-being: financial satisfaction, life satisfaction, and physical health. The study further explores the role of social stratification and the gendered nature of these relationships. The sample (N = 10,235) is restricted to adults 60 years and above, who are retired and answered the survey independently. Multivariate logistic regression analyses indicate that different forms of preparation are positively associated with post-retirement well-being for men and women but socioeconomic resources are positively associated with all three well-being outcomes. Furthermore, for women, there are significant negative interaction effects of income and financial preparation on life satisfaction, as well as negative interaction effects of disability and caregiver preparation on self-rated health. Implications for long-term care, socioeconomic inequality, and gender inequality in paid labor are discussed.