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This Article examines the ways in which inmates are carved out of the protections offered by the Social Security and Medicare systems. By statute, inmates are unable to receive Social Security or disability benefits while incarcerated. Additionally, in many circumstances, their labor does not constitute employment for purposes of calculating quarters of employment for benefits. Therefore, inmates may work their entire prison sentence and, yet, on release discover that they no longer have sufficient years left in their working lives to earn the benefits of Social Security for themselves or their dependents. As the United States grapples with its mass incarceration problem, remedying the narrow issue of Social Security and Medicare entitlement for individuals who are clearly working, and often without the choice of whether to do so, is one way to ease the damage of incarceration on many communities.