Complex health and social care needs of people living in prison with diagnosed or suspected dementia is a growing concern for prisons and prison healthcare staff. The literature is replete with recommendations to better understand the health and social needs of this vulnerable population, to move beyond speculation towards actions to improve their health and well-being. Despite this, there is scant literature exploring the lived care experience of individuals being assessed for or diagnosed with dementia in prisons. The aim of this multi method qualitative study was to investigate how those with suspected dementia were identified, assessed and cared for in Scottish prisons. This article presents case study data from one phase of the larger study. Case studies were constructed from five semi-structured interviews with men with a diagnosed (n = 1) or suspected dementia (n = 4), four semi-structured interviews with staff the men nominated and data from the men’s health care records. The five men had multiple co-morbidities, three had significant mobility issues, two were in receipt of personal care and accommodated in accessible cells. Four of the five men exemplified previous descriptions of older prisoners in that they were socially and physically isolated, and reliant on support with everyday activities. A ‘case by case’ approach to referral, assessment and post diagnostic support was taken by staff who reported a complexity associated with meeting healthcare needs and access to specialist services and supports within a prison regime. This research provides unique and hither to seldom explored insight into the lived care experience of men living with a diagnosed or suspected dementia in prison. The findings have implications for how this marginalised vulnerable group are cared for in prison and on release.