Growing inequities in economic well-being, health, and even life itself pose defining challenges for our times. Using the DYNASIM4 microsimulation model, we project how much older adults’ remaining disability-free and disabled life expectancy, broken into spells with mild and severe disabilities, differ depending on their education and lifetime earnings. We then show older adults’ cumulative Social Security and Medicare contributions and benefits from age 51 through death by disability experience and socio-economic status. We find that people with less education and lower lifetime earnings spend fewer total and disability-free years receiving Social Security and Medicare benefits; greater shares of total benefits are paid during spells of severe disability. Social Security and Medicare thus profoundly protect those with lower lifetime earnings and education. Those with more education and higher earnings have less intensive needs spread over a longer—and growing—period, with Medicare benefits still concentrated in periods of significant disability and health needs. As policymakers consider future Social Security and Medicare changes, they need to consider this diversity in beneficiaries’ experiences and recognize the indispensible insurance protections that these programs provide.