Although there is limited research and evidence base, it is reasonable to expect that high quality information technology is an integral factor in the success of today’s health care sector. However, the health care sector is considered to be low level investor in Information Technology (IT) when compared to other sectors. There are studies that look at the sums spent on health IT as a basis for determining how effective the IT systems are. We support the idea that the effectiveness of IT systems, is not an exact measure and a more systematic approach needs to be taken when evaluating success of an IT system. In this study, we have evaluated an assessment method, which is, “Process Based Information Systems (IS) Effectiveness (PRISE)” based on a novel model of IS effectiveness in the health care sector. The results of our case series provide specific implications concerning the applicability of a general “IS assessment” approach, in the medical context.