Prescription fraud constitutes an important drain of health service resources, but one that is difficult to detect and therefore to prevent or rectify. It is expected that the use of information technology in the prescribing process could enhance fraud prevention and detection. For example, electronic prescribing or networking between prescribing stakeholders could facilitate audit. However, the implementation of several computerized solutions in the British National Health Service (NHS) has been problematic. Computerized support for prescribing and fraud prevention is likely to face similar challenges unless the implementation of a technical solution is considered with due attention to the organizational and social context. This chapter presents the problem of prescription fraud in Britain and some of the technological alternatives available for dealing with the problem. The main focus of the chapter, however, is to consider such technological ‘solutions’ in their broader context and examine how technology may limit or may be limited by organizational and social factors, such as the interests and political considerations of the various stakeholders of the prescribing process. In this respect, the chapter provides a useful analysis within which other information systems security issues can be considered.