This paper explores the likely prevalence of hardship in old age for individuals now nearing retirement. We use two decades of longitudinal data from the Health and Retirement Study to determine what observable demographic, socioeconomic, and financial factors in late middle age predicted economic hardship in old age for the cohort that was nearing retirement age in the mid-1990s. It then uses these findings to predict economic hardship in old age for the cohort nearing retirement age in the mid-2010s. Our analysis suggests that the more recent cohort is likely to realize higher economic insecurity, particularly among men.