The authors examined the impact of a widower's preparedness before his wife's death from cancer on his risk of long-term morbidity. In a population-based study, 691 (76%) of 907 Swedish men who lost a wife to breast, ovarian, or colon cancer in 2000 or 2001 answered an anonymous questionnaire in 2004 or 2005 measuring preparedness at the time of the wife's death and psychological well-being at follow-up. Men aged 38-61 years with a low degree of preparedness at the time of their spouse's death had increased risk of psychological morbidity and other symptoms, such as anxiety (adjusted relative risk (aRR) = 2.1, 95% confidence interval (CI): 1.0, 4.3), a heightened startle response (aRR = 5.3, 95% CI: 1.2, 23.6), emotional numbness (aRR = 2.1, 95% CI: 1.2, 3.6), little or no grief resolution (aRR = 2.7, 95% CI: 1.3, 5.4), and sleep disorders (aRR = 2.3, 95% CI: 1.2, 4.3), 4-5 years after the loss. For older widowers (aged 62-80 years), a low degree of preparedness increased the risk of having repeated painful memories (aRR = 2.8, 95% CI: 1.5, 5.2) and a heightened startle response (aRR = 5.7, 95% CI: 1.5, 21.4) at follow-up. These results show that to improve the long-term psychological well-being of widowers, it may be fruitful to identify care-related facilitators and inhibitors of preparedness.