The older adults most at risk for poverty are those who have experienced cumulative disadvantage as a result of low education attainment, entering the workforce for the first time during an economic recession, health problems that limit their ability to work over long periods of time, and involve extraordinary expenses for either themselves or family members and other vagaries of life. This chapter reviews the social insurance programs that support older Americans, poverty rates, modern retirement compared to “old-fashioned retirement”, gender differences, income equality, and the broad reach of Social Security. It also covers the mechanics of Medicare and Medicaid. There are three Voices in the chapter. One addresses the “comfortable retirement” and its differential meaning and possibility, another focuses on women 50 and over, and the final Perspective piece covers the broad reach of Social Security and its importance to families of all ages.