Last year, 2016, saw the first increase in poverty among individuals aged 65 and over using the Supplemental Poverty Measure (SPM) in 6 years. This paper investigates the underlying causes and explanations of this poverty increase. Utilizing both cross-sectional analyses and a two-year matched sample allows an examination of the shifting demographics of the population aged 65 and over as well as within-family changes across time. By comparing these family and resource compositions between 2014-2015 and 2015-2016, we are able to better identify the factors pushing families with individuals age 65 and older into poverty. We find that a higher share of these families remained in poverty across both 2015 and 2016 than previously, leading to lower rates of mobility out of poverty. Persistent poverty, as well as increases in the share of individuals age 65 and older living in deep poverty, are a cause of concern. Our analyses find that the largest safety net program for older Americans, Social Security, lifted a smaller share of seniors out of poverty in 2016 than in earlier years and that increases in medical expenses among near poor seniors in 2015 are partially responsible for pushing some of these individuals into poverty.