Background: Prisoner populations have a disproportionately high prevalence of risk factors for long-term conditions (LTCs), and movement between community and prisons is a period of potential disruption in the ongoing monitoring and management of LTCs. Method: 19 qualitative interviews with staff, recruited by purposive sampling for professional background, were conducted to explore facilitators and barriers to screening, monitoring and medicines management for LTCs.Results: There is variability in prisoner behaviours regarding bringing community GP-prescribed medication to prison following arrest and detention in police custody, which affects service ability regarding seamless continuation of community prescribing actions. Systems for actively inputting clinical data into existing, nationally agreed, electronic record templates for QOF monitoring are under-developed in prisons and such activity is dependent upon individual “enthusiast(s)”. Similarly, compared to community systems, prison-based systems for “e-prescribing” functionality are under-developed. Conclusion: There is a pressing need to embed standardised QOF monitoring systems within an integrated community/prison commissioning framework, supported by connectivity between prison and community primary care records, including all activity related to QOF compliance. Developing systems for e-prescribing and wider medicines management can improve the quality of care for LTCs. Prison-based general practice has historically not been equivalent to that offered in community settings. Current pressing threats to community equivalence are that QOF monitoring systems are not embedded within prison healthcare payment structures and prison e-prescribing systems are underdeveloped. Supporting wider connectivity between prison and community GP records, including all activity related to QOF compliance and developing systems for e-prescribing had the potential to improve the quality of LTC care for this vulnerable group.