America's prison population is graying fast, and the system built decades ago for young offenders is not built for wheelchairs, dementia, or hospice care. Josh Rushing gets access to jails and prisons around the country to find out what happens when long sentences handed down in the 1980s and 90s catch up with the men serving them. He talks with inmates including Plutarcho Hill, Lewis Young, and Edward Sottile, some of whom have spent more years behind bars than they lived free, and with prison staff running units built specifically to house aging, sick populations. The film lays out the math driving the crisis: keeping an older inmate locked up costs roughly three times as much as a younger one, mostly in medical care, and states are now weighing that cost against public safety as they consider release for prisoners who can barely walk. Officials like Justin Jones speak to the administrative side of a problem nobody designed the system to solve. The result is a look at incarceration as a slow-motion end-of-life crisis rather than a punishment with a fixed endpoint.