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Research on the mental health consequences of solitary confinement has contributed to restrictions on its use, particularly for people with serious mental illness. However, solitary confinement continues to isolate people with physical and mental health problems, even where its use has been restricted. This mixed-methods analysis seeks to evaluate the practice of solitary confinement on mental and physical health using data from a sample of 99 men in Pennsylvania. We first describe patterns of multimorbidity among men in solitary confinement using a latent class analysis to group individuals with shared demographic attributes and mental and physical health conditions. We then use thematic analysis to explore how men from each of these groups experienced and managed health concerns in solitary confinement. Our findings describe significant physical and mental health burdens and unmet healthcare needs. Over three-quarters of respondents reported a physical health diagnosis such as heart disease or diabetes, and over half reported a mental health diagnosis, including anxiety, depression, and schizophrenia. Those with pre-existing, often multiple, health issues struggled to maintain their health given restrictions to daily living, isolated idle time, and limited healthcare access in solitary confinement. These aspects of solitary confinement also challenged those who entered solitary in relatively good health. These findings demonstrate the struggle for self-advocacy in maintaining health and healthcare access under extreme conditions of confinement and point to the need to prevent the health harms of solitary confinement by further restricting its use.