This chapter discusses the extent to which factors known to influence the success and failure of health information systems may be evaluated. More specifically, this is concerned with evaluation of such factors— for screening, diagnostic or preventive purposes—by means of existing evaluation methods designed for users. The author identifies that it is feasible to identify evaluation methods for most success factors and failure criteria. However, there is a need for situational methods engineering as the methods are not dedicated to answering the precise information needs of the project management. Therefore, demands are being placed on the evaluators’ methodical and methodological skills, when evaluating health information systems. The author concludes the chapter by pointing at research needs and opportunities.