Older prisoners are the fastest growing sub-group in the English and Welsh prison estate. They have complex health needs, in spite of which there is a dearth of literature concerning their access to prescribed medication. Literature relating to younger prisoners highlights common issues around maintaining continuity of medication upon reception into prison custody. The objective of the study was to explore the lived experience of older male prisoners regarding continuity of medication upon entry into prison. This paper presents findings from part of a large-scale research project regarding health and social care services for older male adult prisoners. Semi-structured interviews were conducted with male participants (N = 27) aged 60 years and over who had been newly received into prison. Interviews were conducted within the first ten weeks of custody. Participants were asked about their experience of accessing medication on entry into prison. Data were analysed using the constant comparison method. Eighty-five per cent of participants were in receipt of prescribed medication when committed to prison. Older prisoners’ experiences of receiving medication in prison were reflected in four key themes: delays in confirming medicines; changes to medication; communication difficulties; and enforced helplessness. Whilst these experiences mirrored those of prisoners of all ages reported in previous studies, these issues are especially relevant to older prisoners who are likely to have greater and more complex medication needs than their younger peers. In addition, older prisoners experienced unmet needs related to restricted mobility and functional skills that could have impaired their ability to maintain concordance with medication regimes. This study shows that there is need for increased awareness of prescribing issues specific to older prisoners to allay related feelings of anxiety and distress and to ensure they receive appropriate medication.