Life's uncertainties can upend the best-laid retirement plans. Health can fail as people grow older, or their spouses can become ill. Older people can lose their jobs, and often have trouble finding new ones. Marriages can end in widowhood or divorce. Health, employment, and marital shocks near retirement can have serious financial repercussions, raising out-of-pocket medical spending, reducing earnings, disrupting retirement saving, and forcing people to dip prematurely into their nest eggs. This brief examines different types of negative events that can strike near retirement. It reports the incidence of widowhood, divorce, job layoffs, disability, and various medical conditions over a 10-year period, and estimates their impact on household wealth. Data come from the Health and Retirement Study (HRS), a nationally representative survey of older Americans conducted by the University of Michigan for the National Institute on Aging. The survey interviewed a large sample of non-institutionalized adults ages 51 to 61 in 1992 and re-interviewed them every other year. The analysis uses data through 2002, the most recent year available. The results show that many people in their 50s and 60s experience negative shocks that threaten retirement security. Job layoffs, divorce, and the onset of work disabilities near retirement substantially erode retirement savings. The findings highlight the limitations of the safety net when things go wrong in late midlife. This Brief was written for the Center for Retirement Research based at Boston College.