Health information systems (HIS) are a specific area of information systems (IS), where critical patient data is stored and quality health service is only realized with the correct use and efficient dissemination of this data to health workers. Therefore, a balance needs to be established between the levels of security and flow of information on HIS. Instead of implementing higher levels and further mechanisms of control to increase the security of HIS, it is preferable to deal with the arguably weakest link on HIS chain with respect to security: HIS users. In order to provide solutions and approaches for transforming users to the first line of defense in HIS but also to employ capable and appropriate candidates from the pool of newly graduated students, it is important to assess and evaluate the security awareness levels and characteristics of these existing and future users. This study aims to provide a new perspective to understand the phenomenon of security awareness of HIS users with the use of fuzzy analysis, and to assess the present situation of current and future HIS users of a leading medical and educational institution of Turkey, with respect to their security characteristics based on four different security scales. The results of the fuzzy analysis, the guide on how to implement this fuzzy analysis to any health institution and how to read and interpret these results, together with the possible implications of these results to the organization are provided.