Improvements in offender healthcare are key to the current UK Government's reform of the criminal justice system and the aims of reducing reoffending and protecting the public. Current approaches to offender health care emphasise the importance of ‘continuity of care’. Reference to the ‘offender health pathway’ suggests the existence of seamless delivery and experience of care; however, evidence suggests these remain some way off. This research explores prison health discharge planning in four North East prisons and uncovers elements of good practice, but also a number of challenges the prisons continue to face in their attempts to improve clinical pathways for prisoners being released or transferred, including institutional, staffing and prisoner issues. These challenges need to be acknowledged and addressed if robust discharge planning and continuity of care at the end of the offender health pathway is to be achieved.