We use an ongoing longitudinal survey of elderly Taiwanese to examine the linkages among health, the social environment, and exposure to life challenge. Data from three waves of the survey provide measures of social hierarchy, social connection, life challenge, and health outcomes. On the basis of multinomial and binomial logistic models, we explore the effects of social factors and challenge on being unhealthy or deceased at follow-up. The estimates indicate that poor health status at follow-up is associated with (1) low socioeconomic status, not having any living children, limited networks of friends, and low participation in social activities; and (2) three life challenges-chronic financial problems, excessive demands placed by close relatives and friends, and having a spouse in poor health. Respondents facing several challenges or having multiple negative attributes in their social environment are especially likely to be unhealthy at follow-up, although negative attributes appear to be counteracted by positive ones. Many findings from Western societies extend to this Taiwanese population. However, some aspects of social connection and challenge hypothesized to affect health fail to reveal a significant association. The analysis identifies differences between men and women in the effects of specific challenges on health, but sex differences in the effects of socioeconomic status and social connection on health are not significant.