This study investigated the relationship of retirement context and psychological factors with well-being using data on 284 retired married men and women (aged 52-75 years). Measures of retirement context, psychological factors and well-being were used to obtain data from the retirees. Findings show that retirement status, job challenges, financial situation, physical health, activity level, and social support separately predicted psychological well-being. However, there were no significant effects of marital quality and social status on psychological well-being. Results also revealed that preretirement expectations, self efficacy, perceived stress, and optimism separately predicted psychological well-being. Interaction effects of retirement status and job challenges with gender predicted life satisfaction but not depressive symptoms. The results indicate the importance of examining the contextual and psychological factors in understanding the relationship between retirement status and psychological well-being.