Providing adequate health care is particularly complex for healthcare professionals who treat patients in correctional settings. The prison population is particularly vulnerable, both as regards their physical as their mental wellbeing, amongst others due to their social background. Moreover, prison populations contain a high prevalence of persons with addiction problems, mental health issues and diseases. Furthermore, ethical and legal issues such as confidentiality, informed consent of the patient and the perceived or real dual loyalty of health staff to patients and prison authorities play an important role in the organization of adequate health care in prisons. This chapter gives an overview of the legal tensions and incompatibilities between prison legislation and legal provisions relating to qualitative health care in the general population. The latter will draw heavily on the rights of health care patients in a free society, as prison health care is governed by the principle of equivalence, which should ensure that the type and quality of health care delivered to prisoners should be of the same standard as that available in free society. Attention will be paid to contradictions between prison law and the right to adequate health care, as well as contradictions between the organization of health care in prisons and in free society. The report has a rights-based approach, i.e. it offers an analysis of the legal rights prisoners may invoke while in detention to ascertain their right to qualitative health-care. This implies that the legal provisions discussed will mainly stem from laws such as the 2005 Basic Law on prisons. Circular letters, directed at the internal organization of prisons, do not enumerate new rights for prisoners, nor can prisoners use them to enforce the provisions contained therein. Moreover, as a rule, they are not made public. As such, they are discussed to clarify certain aspects rather than being discussed exhaustively.