I pray every night that I die in my sleep."Two patients said these words to my medical student on the same morning during rounds recently at the prison hospital. One was confined to a hospital room for months because he required intensive wound care; the other, a man with paraplegia and depression, was similarly isolated and sent to the prison hospital because his local jail could not manage his medical care. Many would rather die than live in these circumstances.In a prison, the list of grievances is long: solitary confinement for some, too few rehabilitative opportunities, difficulty communicating with loved ones, insufficient attention to medical needs, victimization, poor nutrition, and worst of all, abasement and dehumanization. People with chronic health conditions exist in a system designed for punishment, control, and security, not health care.Injustice permeates the carceral system and the larger criminal legal apparatus. My students routinely hear about trial delays, an inability to afford bond as a precursor to incarceration, rushed plea deals, and inadequate legal representation as pre-incarceration issues. Post-incarceration, people may return to communities in which poverty is concentrated, substance use is endemic, and educational outcomes are poorer. These inequities in structural and social determinants of health increase the risk of reincarceration. Further, systemic racism in American society ensures that people of color are "disproportionately targeted for arrest, conviction, and incarceration" [1]. A patient who leaves the prison hoping never to come back sadly meets the next student or resident on service.Bringing learners into this environment thus poses many challenges. Here, the difficulty in question is not a bureaucratic hurdle or safety concern, but rather moral distress, born of the near-daily anguish of hearing stories of injustice, witnessing unjust acts or neglect, or encountering dehumanization in all its cruelty.