We explore debt and debt management among older Americans (ages 51–61 years) using the 2018 National Financial Capability Study. Though these individuals should have been at the peak of their retirement savings, we show that many were heavily indebted, often due to unpaid medical bills and student loans. Additionally, fewer than half (43%) could correctly answer three basic financial literacy questions; importantly, less financially literate people were more likely to hold excessive debt, be contacted by debt collectors, and carry medical debt or student loans. Our findings show that, even before the pandemic, a sizable proportion of older Americans was financially distressed, underscoring the need for researchers and policymakers to devote attention to specific types of debt that burden the older population. Particularly vulnerable groups include African-Americans, women, and the least-educated.